10a-AZALIDE COMPOUND

Abstract

 [Object]: To provide a compound having a novel structure effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria.
[Solution]: A novel 10a-azalide compound represented by the formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof, or an intermediate for the preparation of the same. The compound of the present invention has superior antibacterial activity against Hemophilus influenzae, erythromycin resistant pneumococci and the like, and therefore, the compound can be used as a therapeutic agent of infectious diseases.

Description

Technical Field

[0001] The present invention relates to a novel antibiotic having an erythromycin-like structure.

Background Art

[0002] Erythromycin A is an antibiotic which has been widely used as a therapeutic agent for infectious diseases caused by gram positive bacteria, mycoplasmas, and the like. However, due to decomposition by gastric acid, erythromycin has a drawback of inconstant pharmacokinetics. Therefore, derivatives of erythromycin having increased stability to acids were researched. As a result, macrolides having stable pharmacokinetics such as clarithromycin, azithromycin (Patent documents 1 and 2 mentioned below) and roxithromycin have been developed. These macrolide agents have been applied in a therapeutic field of respiratory infectious diseases of ambulatory patients, and therefore, they are required to have a potent antibacterial activity especially against pneumococci, streptococci, and Hemophilus influenzae which are frequently isolated clinically. Furthermore, since macrolide-resistant pneumococci have been highly frequently isolated from community acquired pneumonia patients, it has been considered important that they are effective against the resistant pneumococci.

[0003] As a result of various researches in recent years, Agouridas et al. found HMR3647 (telithromycin, Patent document 3 mentioned below) in 1995, and successively Or et al. found ABT-773 (cethromycin, Patent document 4 mentioned below) in 1998 as macrolides that are effective both against erythromycin resistant pneumococci and erythromycin resistant streptococci. Then, 2-fluoroketolide (Patent document 5 mentioned below) of which efficacy was further enhanced was reported.

[0004] From a structural viewpoint, marketed macrolides are mainly classified into 14-membered or 15-membered ring type macrolides which are erythromycin derivatives, and 16-membered ring type macrolides which are leucomycin derivatives. Among the erythromycin derivatives, the 15-membered ring macrolides include azithromycin mentioned above. Azithromycin, unlike the other 14-membered ring macrolides, possesses a structural feature of having a nitrogen atom in the lactone ring, and therefore the macrolide is called azalide. Nomenclature of azalides is based on the position number of a carbon atom substituted with a nitrogen atom when the carbonyl group of the lactone is assumed to be in the 1-position. In the case of azithromycin mentioned above, since the nitrogen atom is introduced in the position of the ninth carbon atom from the carbonyl group, the compound is called 9a-azalide.

[0005] In addition to the 9a-azalides, 8a-azalides (Patent document 6 mentioned below) and lla-azalides (Patent document 7 mentioned below) are known as examples of reported azalides obtainable by chemical conversion of 14-membered ring macrolides.

[0006] As for 10a-azalides, those derived from 16-membered ring macrolides as leucomycin derivatives have recently been reported (Patent document 8 mentioned below). However, no 10a-azalides derived from 14-membered ring macrolides have been reported.

[0007] 

Patent document 1: U.S. Patent No. 4,474,768

Patent document 2: U.S. Patent No. 4,517,359

Patent document 3: EP680967

Patent document 4: WO98/09978

Patent document 5: WO02/32919

Patent document 6: EP508726

Patent document 7: WO2003/014136

Patent document 8: WO2005/019238

Disclosure of the Invention

Object to be Achieved by the Invention

[0008] An object of the present invention is to provide a compound having a novel structure which is effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria.

Means for Achieving the Object

[0009] The inventors of the present invention conducted various researches on azalide compounds, and as a result, succeeded in synthesis of novel azalides derived from 14-membered ring macrolides.
More specifically, the inventors of the present invention used 14-membered ring macrolides as starting materials, and oxidized 10-oxo compounds, which were obtained by oxidative cleavage of the diol moieties in the 11- and 12-positions, to derive into carboxyl compounds. Then, they performed rearrangement reactions by using the carboxyl compounds as starting materials to synthesize compounds having 10-amino group which were not reported so far. Further, by performing partial structural conversion and then intramolecular cyclization of those compounds, they succeeded in providing 10a-azalide compounds having a novel skeleton.

[0010] Further, as a result of evaluation of antibacterial activity thereof compounds, the inventors found that the 10a-azalide compounds had activities superior to those of the erythromycin derivatives as the starting materials, and accomplished the present invention.

[0011] The present invention thus relates to a 10a-azalide compound represented by the formula (I):

[0012] 

[0013] {wherein, in the formula (I), R¹ is:
hydrogen atom,
a halogen atom, or
a C₁-₁₀ alkyl group which may be substituted,

[0014] R² and R³ combine together to represent oxo group, or
one of them is hydrogen atom, and the other is:

hydrogen atom,

hydroxyl group,

a protected hydroxyl group,

a group represented by the formula -X⁰³¹-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-A⁰³³-X⁰³⁴-R⁰³¹,

or a group represented by the formula:

[0015] 

[0016] wherein X⁰³¹ is:

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OHO₂-, or

a group represented by the formula -OCON(R²⁰)-,

one of R³² and R³³ is hydrogen atom, and the other is:

hydrogen atom,

amino group,

hydroxyl group,

a protected hydroxyl group,

a group represented by the formula -OCON(R²⁴)R²⁵ (in the formula, R²⁴ and R²⁵ both represent hydrogen atom, or represent groups which combine to form a cyclic amino group together with the adjacent nitrogen atom),

a group represented by the formula -X³³¹-R³³¹,

a group represented by the formula -X³³¹-A³³¹-X³³²-R³³¹,

a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-R³³¹, or

a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-A³³³-X³³⁴-R³³¹,
wherein X³³¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-,

a group represented by the formula -OCON(R²⁰)-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-,

[0017] or one of R³² and R³³ is hydroxyl group, and the other is:

a group represented by the formula -CH₂NH₂,

a group represented by the formula -X³³⁵-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-R³³², or

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-A³³⁶-X³³⁸-R³³²,
wherein X³³⁵ is:

a single bond,

a group represented by the formula -(CH₂)_n-N(R²⁰)-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CO-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CO₂-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CON(R²¹)-,

a group represented by the formula -(CH₂)_n-N(R²⁰)O-,

a group represented by the formula -(CH₂)_n-OCON(R²⁰)-,

a group represented by the formula -(CH₂)_n-ON(R²⁰)CO-,

a group represented by the formula -(CH₂)_n-O-,

a group represented by the formula -(CH₂)_n-OCO-,

a group represented by the formula -(CH₂)_n-OCO₂-,

a group represented by the formula -(CH₂)_n-OC(NR²⁰)-, or

a group represented by the formula -(CH₂)_n-S(O)_p-,

[0018] or R³² and R³³ combine together to represent:

oxo group,

oxime group,

a group represented by the formula =N-X³³⁹-R³³³,

a group represented by the formula =N-X³³⁹ -A³³⁷ -X³⁴⁰-R³³³,

a group represented by the formula =N-X³³⁹-A³³⁷ -X³⁴⁰-A³³⁸-X³⁴¹-R³³³,

a group represented by the formula =N-X³³⁹-A³³⁷-X³⁴⁰-A³³⁸-X³⁴¹-A³³⁹-X³⁴²-R³³³, or a group represented by the formula:

[0019] 

[0020] wherein X³³⁹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-, and

R³³⁴ is:

a group represented by the formula -SH,

a group represented by the formula -OH,

a group represented by the formula -X³⁴³-R³³⁵,

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-R³³⁵,

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-A³⁴¹-X³⁴⁵-R³³⁵, or

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-A³⁴¹-X³⁴⁵-A³⁴²-X³⁴⁶-R³³⁵,
wherein X³⁴³ is:

a single bond,

a group represented by the formula -S-, or

a group represented by the formula -(CH₂)_nCO-,

R⁴ is:

hydrogen atom,

a group represented by the formula -CONHCO₂Me

a group represented by the formula -X⁰⁴¹-R⁰⁴¹,

a group represented by the formula -X⁰⁴¹-A⁰⁴¹-X⁰⁴²-R⁰⁴¹,

a group represented by the formula -X⁰⁴¹-A⁰⁴¹-X⁰⁴²-A⁰⁴²-X⁰⁴³-R⁰⁴¹, or

a group represented by the formula -X⁰⁴¹-R⁰⁴¹-X⁰⁴²-A⁰⁴²-X⁰⁴³-A⁰⁴³-X⁰⁴⁴-R⁰⁴¹,
wherein X⁰⁴¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CON(R²⁰)-, or

a group represented by the formula -CO₂-,

or R⁴ may combine with R⁶ to form cyclic carbonate [-CO₂-],

[0021]  one of R⁵ and R⁶ is hydrogen atom, and the other is:

hydrogen atom,

hydroxyl group,

a protected hydroxyl group,

amino group,

a protected amino group,

a halogen atom,

a group represented by the formula -OCONH₂,

a group represented by the formula -X⁰⁶¹-R⁰⁶¹,

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-R⁰⁶¹,

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-R⁰⁶¹, or

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-A⁰⁶³-X⁰⁶⁴-R⁰⁶¹,

or may combine with R⁷ to form cyclic carbamate [-OCO-],
wherein X⁰⁶¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-,

a group represented by the formula -OCON(R²⁰)-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-,

a group represented by the formula -N(R²⁰)SO₂-, or

a group represented by the formula -CH₂N(R²⁰)-,

or R⁵ and R⁶ combine together to represent

oxo group,

oxime group,

a group represented by the formula =N-NH₂,

a protected oxime group,

a group represented by the formula =N-X⁰⁶⁵-R⁰⁶²,

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-R⁰⁶²,

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-R⁰⁶², or

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-A⁰⁶⁶-X⁰⁶⁸-R⁰⁶²

wherein X⁰⁶⁵ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-,

[0022] R⁷ is:

hydrogen atom,

hydroxyl group,

a protective group of amino group,

a group represented by the formula -X⁰⁷¹-R⁰⁷¹,

a group represented by the formula -X⁰⁷¹-A⁰⁷¹-X⁰⁷²-R⁰⁷¹, or

a group represented by the formula -X⁰⁷¹-A⁰⁷¹-X⁰⁷²-R⁰⁷²-X⁰⁷³-R⁰⁷¹, or may combine with R¹⁰ to form cyclic carbamate [-CO₂CH₂-],
wherein X⁰⁷¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -SO₂-,

[0023] R⁸ and R⁹, which are the same or different, represent:

hydrogen atom,

a group represented by the formula -X⁰⁸¹-R⁰⁸¹,

a group represented by the formula -X⁰⁸¹-A⁰⁸¹-X⁰⁸²-R⁰⁸¹, or

a group represented by the formula -X⁰⁸¹-A⁰⁸¹-X⁰⁸²-A⁰⁸²-X⁰⁸³-R⁰⁸¹,
wherein X⁰⁸¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

[0024] R¹⁰ and R¹¹, which are the same or different, represent
hydrogen atom,
a group represented by the formula -X¹⁰¹-R¹⁰¹,
a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-R¹⁰¹,
a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-A¹⁰²-X¹⁰³-R¹⁰¹, or
a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-A¹⁰²-X¹⁰³-A¹⁰³-X¹⁰⁴-R¹⁰¹,
wherein X¹⁰¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

[0025] R¹² is:

hydrogen atom,

a protective group of hydroxyl group,

a group represented by the formula -X¹²¹-R¹²¹,

a group represented by the formula -X¹²¹-A¹²¹-X¹²²-R¹²¹, or

a group represented by the formula -X¹²¹-A¹²¹-X¹²²-A¹²²-X¹²³-R¹²¹,
wherein X¹²¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

[0026] R¹³ and R¹⁴, which are the same or different, represent
hydrogen atom,
a protective group of amino group,
a group represented by the formula -X¹³¹-R¹³¹,
a group represented by the formula -X¹³¹-A¹³¹-X¹³²-R¹³¹, or
a group represented by the formula -X¹³¹-A¹³¹-X¹³²-A¹³²-X¹³³-R¹³¹,
wherein X¹³¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

[0027] R¹⁵ is:
hydrogen atom,
hydroxyl group,
a protected hydroxyl group,
a group represented by the formula -X¹⁵¹-R¹⁵¹,
a group represented by the formula -X¹⁵¹-A¹⁵¹-X¹⁵²-R¹⁵¹, or
a group represented by the formula -X¹⁵¹-A¹⁵¹-X¹⁵²-A¹⁵²-X¹⁵³-R¹⁵¹,
wherein X¹⁵¹ is:

a single bond,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-, or

a group represented by the formula -OCON(R²⁰)-,

[0028] X⁰³², X⁰³³, X⁰³⁴, X³³², X³³³, X³³⁴, X³³⁶, X³³⁷, X³³⁸, X³⁴⁰, X³⁴¹, X³⁴², X³⁴⁴, X³⁴⁵, X³⁴⁶, X⁰⁴², X⁰⁴³, X⁰⁴⁴, X⁰⁶², X⁰⁶³, X⁰⁶⁴, X⁰⁶⁶, X⁰⁶⁷, X⁰⁶⁸, X⁰⁷², X⁰⁷³, X⁰⁸², X⁰⁸³, X¹⁰², X¹⁰³, X¹⁰⁴, X¹²², X¹²³, X¹³², X¹³³, X¹⁵² and X¹⁵³ mentioned above, which are the same or different, represent
a single bond
a group represented by the formula -O-,
a group represented by the formula -OCO-,
a group represented by the formula -OCO₂-,
a group represented by the formula -OCON(R²⁰)-,
a group represented by the formula -S(O)_p-,
a group represented by the formula -SO₂N(R²⁰)-,
a group represented by the formula -OCS-,
a group represented by the formula -CO-,
a group represented by the formula -CO₂-,
a group represented by the formula -CON(R²⁰)-,
a group represented by the formula -CH=N-,
a group represented by the formula -CH=N-O-,
a group represented by the formula -CH=N(R²⁰)-,
a group represented by the formula -CH=N(R²⁰)O-,
a group represented by the formula -CH=N(R²⁰)N(R²¹)-,
a group represented by the formula -CH=N(OR²⁰)-,
a group represented by the formula -CH=N-N(R²⁰)R²¹-,
a group represented by the formula -CS-,
a group represented by the formula -C(S)O-,
a group represented by the formula -CSN(R²⁰)-,
a group represented by the formula -O-N=CH-,
a group represented by the formula -N=CH-,
a group represented by the formula -N(R²⁰)-,
a group represented by the formula -N(R²⁰)CO-,
a group represented by the formula -N(R²⁰)CS-,
a group represented by the formula -N(R²⁰)SO₂-,
a group represented by the formula -N(R²⁰)CO₂-, or
a group represented by the formula -N(R²⁰)CON(R²¹)-,

[0029] A⁰³¹, A⁰³², A⁰³³, A³³¹, A³³², A³³³, A³³⁴, A³³⁵, A³³⁶, A³³⁷, A³³⁸, A³³⁹, A³⁴⁰, A³⁴¹, A³⁴², A⁰⁴¹, A⁰⁴², A⁰⁴³, A⁰⁶¹, A⁰⁶², A⁰⁶³, A⁰⁶⁴, A⁰⁶⁵, A⁰⁶⁶, A⁰⁷¹, A⁰⁷², A⁰⁸¹, A⁰⁸², A¹⁰¹, A¹⁰², A¹⁰³, A¹²¹ A¹²², A¹³¹, A¹³², A¹⁵¹ and A¹⁵² mentioned above, which are the same or different, represent
a divalent C_1-10 aliphatic hydrocarbon group which may be substituted with hydroxyl group,
an arylene group, or
a divalent heterocyclic group,

[0030] R⁰³¹, R³³¹, R³³², R³³³, R³³⁵, R⁰⁴¹, R⁰⁶¹, R⁰⁶², R⁰⁷¹, R⁰⁸¹, R¹⁰¹, R¹²¹, R¹³¹ and R¹⁵¹ mentioned above, which are the same or different, represent
a C_1-10 alkyl group which may be substituted,
a C_2-10 alkenyl group which may be substituted,
a C_2-10 alkynyl group which may be substituted,
a C_2-10 cycloalkyl group which may be substituted,
a C_3-10 cycloalkyl group condensed with an aryl group, which may be substituted,
an aryl group which may be substituted, or
a heterocyclic group which may be substituted,

[0031] substituents of the groups "which may be substituted" mentioned above each mean arbitrary 1 to 5 substituents selected from the following group of substituents, and the group of substituents consists of:

• carboxyl group,
• a halogen atom,
• oxo group,
• hydroxyl group,
• cyano group,
• nitro group,
• oxido group,
• sulfonic acid group, and
• thiol group,

as well as the following group which may be substituted with groups of the group A:

• a C_1-10 alkyl group,
• a C_2-12 alkenyl group,
• a C_2-12 alkynyl group,
• a C_3-10 cycloalkyl group,
• a C_1-10 alkoxy group,
• a C_1-10 hydroxyalkoxy group,
• a C_2-12 alkenyloxy group,
• a carboxy(C_1-6 alkyloxy) group,
• a cyano(C_1-6 alkyloxy) group,
• a C_1-10 alkylthio group,
• a C_1-6 alkylsulfonyl group,
• an arylsulfonyl group which may be substituted with a C_1-6 alkyl group or a halogen atom,
• a C_1-10 haloalkylthio group,
• a C_2-10 alkenylthio group,
• a (C_1-6 alkoxy)(C_1-6 alkyl) group,
• a (C_1-6 alkoxy)(C_1-6 alkoxy) group,
• a C_1-10 haloalkyl group,
• a C_2-12 alkanoyl group,
• a C_2-12 alkanoyloxy group,
• a (C_2-12 alkanoyloxy)(C_1-6 alkyl) group,
• a benzoyl group which may be substituted with 1 to 3 of halogen atoms or nitro groups,
• a C_2-6 alkanoylamino group,
• an aminosulfonyl group which may be substituted with 1 or 2 of C_1-6 alkyl groups,
• a C_1-6 alkylsulfonyl group,
• a C_1-6 alkylsulfonylamino group,
• a benzenesulfonylamino group which may be substituted with C_1-6 alkyl,
• succinimido group,
• maleimido group,
• phthalimido group,
• a C_2-10 alkoxycarbonyl group,
• a C_2-10 alkoxycarbonylalkoxy group,
• tri-(C_1-6 alkyl)silyloxy group,
• a group represented by the formula -N(R²²)R²³ (in the formula, R²² and R²³ each represent hydrogen atom, a C_1-6 alkyl group, a C_1-6 hydroxyalkyl group, a C_3-10 alkoxycarbonylalkyl group or a cyano(C_1-6 alkyl) group, or represent groups which combine to form, together with the adjacent nitrogen atom, a cyclic amino group, which may be substituted with "a C_1-6 alkyl group, a cyano(C_1-6 alkyl) group, a C_3-10 cycloalkyl group, a C_2-6 alkanoyl group, benzoyl group, an aryloxy(C_2-6 alkanoyl) group which may be substituted with "a C_1-6 alkyl group or a C_1-6 alkoxy group", a (C_1-6 alkoxy)(C_1-6 alkyl) group, a C_2-6 alkoxycarbonyl group, oxo group, or hydroxyl group"),
• a group represented by the formula -CON(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),
• a group represented by the formula -OCON(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),
• a group represented by the formula -CH₂N(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),
• a group represented by the formula -O(CH₂)_mN(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above), and
• "an aryl group, a heterocyclic group, an aryloxy group, an arylthio group, a heterocyclyloxy group or a heterocyclylthio group" which may be substituted with 1 to 5 of groups arbitrarily selected from the group consisting of "a C_1-6 alkyl group, a C_1-6 haloalkyl group, a halogen atom, a C_1-6 alkoxy group, an aminosulfonyl group which may be substituted with 1 or 2 of C_1-6 alkyl groups, an aminosulfonylamino group which may be substituted with 1 or 2 of C_1-6 alkyl groups, an amino(C_1-6 alkyl) group which may be substituted with 1 or 2 of C_1-6 alkyl groups, a saturated heterocyclic group, a C_1-6 alkyl group substituted with a saturated heterocyclic group, carboxyl group, a C_2-10 alkoxycarbonyl group, a C_1-6 hydroxyalkyl group, cyano group, a cyano(C_1-6 alkyl) group, an amino group which may be substituted with 1 or 2 of C_1-6 alkyl groups, hydroxyl group, a C_1-10 alkylthio group, a C_1-6 alkylsulfonyl group, a C_1-6 alkylsulfonylamino group and nitro group",

wherein group A consists of "an aryl group, a heterocyclic group, a heterocyclylthio group or an aryloxy group" which may be substituted with "a halogen atom, a C_1-6 alkyl group, a hydroxy(C_1-6 alkyl) group, hydroxyl group or nitro group", cyano group, cyanothio group, carboxyl group, hydroxyl group, a C_2-10 alkoxycarbonyl group, and a C_1-10 alkoxy group,

[0032] R²⁰ and R²¹ mentioned above, which are the same or different, represent
a group suitably selected from hydrogen atom, and a C_1-10 alkyl group which may be substituted with the aforementioned substituents,

[0033] p mentioned above is an integer of 0 to 2,
n mentioned above is 1 or 2, and
m mentioned above is an integer of 2 to 4}, a pharmaceutically acceptable salt thereof, or a solvate thereof.

[0034] The present invention also relates to a compound represented by the formula (II), which is an intermediate for the synthesis of a 10a-azalide compound having superior antibacterial activity:

[0035] 

[0036] (in the formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R¹², R¹³, R¹⁴ and R¹⁵ have the same meanings as those defined above except for the case where R⁶ and R⁷ combine together to form cyclic carbamate [-OCO-]).

[0037] In the present invention, the symbol "C_x-y " means that the group mentioned after that has x to y of carbon atoms.
Examples of the "halogen atom" include fluorine, chlorine, bromine, and iodine.
The "C_1-6 alkyl group" is a linear or branched alkyl group having 1 to 6 carbon atoms, and examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, 1,1-dimethylpropyl group, n-hexyl group, and the like.

[0038] The "C_1-10 alkyl group" is a linear or branched alkyl group having 1 to 10 carbon atoms, and examples include, for example, the aforementioned specific examples of the "C_1-6 alkyl group", as well as, for example, 1,1,3,3-tetramethylbutyl group, n-nonanyl group, n-decanyl group, and the like.

[0039] The "C_2-10 alkenyl group" is a linear or branched alkenyl group having 2 to 10 carbon atoms corresponding to the aforementioned "alkyl group" having one or more double bonds at arbitrary positions, and examples include, for example, vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-butenyl group, 1,3-butadienyl group, 2-pentenyl group, 3-pentenyl group, 2-hexenyl group, and the like.

[0040] The "C_2-10 alkynyl group" means a linear or branched alkynyl group having 2 to 10 carbon atoms corresponding to the aforementioned "alkyl group" having one or more triple bonds at arbitrary positions, and examples include, for example, ethynyl group, 1-propynyl group, 2-propynyl group, and the like.

[0041] The "C_1-10 haloalkyl group" is an alkyl group corresponding to the aforementioned "C_1-10 alkyl group" substituted with one or two or more halogen atoms, and examples of include, for example, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, perfluorohexyl group, and the like.

[0042] The "C_1-6 alkoxy group" is a linear or branched alkoxy group having 1 to 6 carbon atoms, and examples include, for example, methoxy group, ethoxy group, 1-propoxy group, isopropoxy group, 1-butoxy group, 1-methyl-1-propoxy group, t-butoxy group, 1-pentyloxy group, and the like.

[0043] The "C_1-10 alkoxy group" is a linear or branched alkoxy group having 1 to 10 carbon atoms, and examples include, for example, besides the specific examples of the aforementioned "C_1-6 alkoxy group", for example, 1,1,3,3-tetramethylbutoxy group, n-decyloxy group, and the like.

[0044] The "C_2-10 alkoxycarbonyl group" means a group having 2 to 10 carbon atoms formed by binding the aforementioned alkoxy group and carbonyl group, and examples include, for example, methoxycarbonyl group, ethoxycarbonyl group, t-butoxycarbonyl group, and the like.

[0045] The "aryl group" is a monocyclic to tetracyclic aromatic carbon ring group having 6 to 18 carbon atoms, and examples include, for example, phenyl group, naphthyl group, anthryl group, phenanthrenyl group, tetracenyl group, pyrenyl group, and the like.

[0046] The "heterocyclic group" is a monocyclic heterocyclic group, or a condensed ring type heterocyclic group containing 1 to 5 of atoms arbitrarily selected from nitrogen atom, oxygen atom and sulfur atom as ring constituting atoms, and includes a saturated heterocyclic group, an aromatic heterocyclic group, a partially saturated monocyclic aromatic heterocyclic group and a condensed ring type heterocyclic group comprising an aromatic heterocyclic group having a single partially saturated ring. The condensed ring type heterocyclic group having a single partially saturated ring may be substituted with oxo group. When the hetero atom is sulfur atom, dioxide compounds also fall within the scope of the present invention.
As the heterocyclic group, a heterocyclic group having 2 to 10 carbon atoms in the ring system is preferred.
In this specification, a "heterocyclic group" is also referred to as "heterocyclyl group" for convenience, and these have the same meaning.

[0047] Examples of the "saturated heterocyclic group" include, for example, aziridinyl group, azetidinyl group, pyrrolidinyl group, imidazolidinyl group, pyrazolidinyl group, oxolanyl group, thiolanyl group, piperidinyl group, oxazolidinyl group, isoxazolidinyl group, piperazinyl group, oxanyl group, thianyl group, morpholinyl group, thiomorpholinyl group, and the like.

[0048] Examples of the "aromatic heterocyclic group" include, for example, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, quinolyl group, isoquinolyl group, thienyl group (e.g., 2-thienyl group, 3-thienyl group), pyrrolyl group (e.g., 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group), thiazolyl group (e.g., 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group), isothiazolyl group (e.g., 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group), pyrazolyl group (e.g., 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group), imidazolyl group (e.g., 1-imidazolyl group, 2-imidazolyl group, 3-imidazolyl group), furyl group (e.g., 2-furyl group, 3-furyl group), oxazolyl group (e.g., 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group), isoxazolyl group (e.g., 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group), oxadiazolyl group (e.g., 1,2,3-oxadiazolyl group, 1,3,4-oxadiazolyl group), thiadiazolyl group (e.g., 1,2,3-thiadiazolyl group, 1,3,4-thiadiazolyl group), triazolyl group (e.g., 1,2,4-triazolyl group), benzofuranyl group (e.g., 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group), benzothienyl group (e.g., 2-benzothienyl group, 3-benzothienyl group, 4-benzothienyl group, 5-benzothienyl group), indolyl group (e.g., 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group), benzoxazolyl group (e.g., 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group), benzisoxazolyl group (e.g., 3-benzo[c]isoxazolyl group, 4-benzo[c]isoxazolyl group, 5-benzo[c]isoxazolyl group, 6-benzo[c]isoxazolyl group, 3-benzo[d]isoxazolyl group, 4-benzo[d]isoxazolyl group, 5-benzo[d]isoxazolyl group, 6-benzo[d]isoxazolyl group), indazolyl group (e.g., 3-indazolyl group, 4-indazolyl group, 5-indazolyl group, 6-indazolyl group), benzimidazolyl group (e.g., 2-benzimidazolyl group, 4-benzimidazolyl group, 5-benzimidazolyl group, 6-benzimidazolyl group), benzoxadiazolyl group (e.g., 4-benzo[1,2,5]oxadiazolyl group, 5-benzo[1,2,5]oxadiazolyl group, 4-benzo[1,2,3]oxadiazolyl group, 5-benzo[1,2,3]oxadiazolyl group), benzothiadiazolyl group (e.g., 4-benzo[1,2,5]thiadiazolyl group, 5-benzo[1,2,5]thiadiazolyl group, 4-benzo[1,2,3] thiadiazolyl group, 5-benzo[1,2,3]thiadiazolyl group), indolidinyl group (e.g., 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group), thienopyridyl group (e.g., 2-thieno[2,3-b]pyridyl group, 3-thieno[2,3-b]pyridyl group, 5-thieno[2,3-b]pyridyl group, 6-thieno[2,3-b]pyridyl group, 2-thieno[3,2-b]pyridyl group, 3-thieno[3,2-b]pyridyl group, 5-thieno[3,2-b]pyridyl group, 6-thieno[3,2-b]pyridyl group), pyrazolopyridyl group (e.g., 2-pyrazolopyridyl group, 3-pyrazolopyridyl group, 5-pyrazolopyridyl group, 6-pyrazolopyridyl group), imidazopyridyl group (e.g., 1-imidazo[1,5-a]pyridyl group, 3-imidazo[1,5-a]pyridyl group, 5-imidazo[1,5-a]pyridyl group, 7-imidazo[1,5-a]pyridyl group, 2-imidazo[1,2-a]pyridyl group, 3-imidazo[1,2-a]pyridyl group, 5-imidazo[1,2-a]pyridyl group, 7-imidazo[1,2-a]pyridyl group), imidazopyrazyl group (e.g., 1-imidazo[1,5-a]pyrazyl group, 3-imidazo[1,5-a]pyrazyl group, 5-imidazo[1,5-a]pyrazyl group, 8-imidazo[1,5-a]pyrazyl group, 2-imidazo[1,2-a]pyrazyl group, 3-imidazo[1,2-a]pyrazyl group, 5-imidazo[1,2-a]pyrazyl group, 8-imidazo[1,2-a]pyrazyl group), pyrazolopyrimidyl group (e.g., 2-pyrazolo[1,5-a] pyrimidyl group, 3-pyrazolo[1,5-a]pyrimidyl group, 5-pyrazolo[1,5-a]pyrimidyl group, 6-pyrazolo[1,5-a]pyrimidyl group, 2-pyrazolo[1,5-c]pyrimidyl group, 3-pyrazolo[1,5-c] pyrimidyl group, 4-pyrazolo[1,5-c]pyrimidyl group, 5-pyrazolo[1,5-c]pyrimidyl group), triazolopyrimidyl group (e.g., 3-[1,2,3]triazolo[1,5-a]pyrimidyl group, 5-[1,2,3]triazolo[1,5-a]pyrimidyl group, 6-[1,2,3]triazolo[1,5-a]pyrimidyl group, 3-[1,2,3]triazolo[1,5-c]pyrimidyl group, 4-[1,2,3]triazolo[1,5-c]pyrimidyl group, 5-[1,2,3]triazolo[1,5-c]pyrimidyl group, 2-[1,2,4]triazolo[1,5-a]pyrimidyl group, 5-[1,2,4]triazolo[1,5-a]pyrimidyl group, 6-[1,2,4]triazolo[1,5-a]pyrimidyl group, 7-[1,2,4]triazolo[1,5-a]pyrimidyl group, 2-[1,2,4]triazolo[1,5-c]pyrimidyl group, 5-[1,2,4]triazolo[1,5-c]pyrimidyl group, 7-[1,2,4]triazolo[1,5-c]pyrimidyl group, 8-[1,2,4]triazolo[1,5-c]pyrimidyl group), thienothienyl group (e.g., 2-thieno[2,3-b]thienyl group, 3-thieno[2,3-b]thienyl group, 2-thieno[3,2-b]thienyl group, 3-thieno[3,2-b]thienyl group), imidazothiazolyl group (e.g., 2-imidazo[2,1-b]thiazolyl group, 3-imidazo[2,1-b]thiazolyl group, 5-imidazo[2,1-b]thiazolyl group, 2-imidazo[5,1-b]thiazolyl group, 3-imidazo[5,1-b]thiazolyl group, 5-imidazo[5,1-b]thiazolyl group), and the like.

[0049] Examples of the "partially saturated monocyclic aromatic heterocyclic group and condensed ring type heterocyclic group comprising an aromatic heterocyclic group having a single partially saturated ring" include, for example, maleimido group, tetrahydrobenzofuranyl group, tetrahydrobenzothienyl group, tetrahydrobenzopyrrolyl group, 2,3-dihydro-1H-benzofuranyl group, 2,3-dihydro-1H-benzothienyl group, 2,3-dihydro-1H-indolyl group, 2,3-dihydro-1H-indazolyl group, 2,3-dihydro-1H-benzotriazolyl group, 2,3-dihydro-1H-benzoxazolyl group, 2,3-dihydro-1H-benzothiazolyl group, benzo[1,3]oxathioly group, benzo[1,3]dioxolyl group, 2H-chromenyl group, cromanyl group, indolinyl group, isoindolinyl group, and the like.

[0050] Examples of the "condensed ring type heterocyclic group having a partially saturated monocyclic ring and substituted with oxo group" include, for example, 2-oxo-1,3-dihydro-1H-indolyl ring, 3-oxo-1,2-dihydro-1H-indazolyl ring, 2-oxo-3H-benzoxazolyl ring, 2-oxo-3H-benzothiazolyl ring, 2-oxo-benzo[1,3]oxathiolyl ring, 2-oxo-benzo[1,3]dioxolyl ring, 2-oxo-chromenyl ring, and the like.

[0051] The "C_3-10 cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms, and examples include, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, adamantyl group, and the like.

[0052] The "C_2-12 alkanoyl group" is a linear or branched alkanoyl group having 2 to 12 carbon atoms, and examples include, for example, acetyl group, propionyl group, isopropionyl group, butyryl group, pivaloyl group, and the like.
The "C_2-12 alkanoyloxy group" means a group formed by binding the aforementioned C_2-12 alkanoyl group and oxy group, and examples include, for example, acetyloxy group, propionyloxy group, pivaloyloxy group, and the like.

[0053] The "(C_2-12 alkanoyloxy)(C_1-6 alkyl) group" means a group formed by binding the aforementioned C_2-12 alkanoyloxy group and C_1-6 alkyl group, and examples include, for example, acetyloxyethyl group, propionyloxymethyl group, pivaloyloxymethyl group, and the like.
The "C_2-6 alkanoylamino group" means a group formed by binding the aforementioned C_2-6 alkanoyl group and amino group, and examples include, for example, acetylamino group, propionylamino group, pivaloylamino group, and the like.

[0054] The "(C_1-6 alkoxy)(C_1-6 alkoxy) group" means a group formed by binding two of the aforementioned C_1-6 alkoxy groups, and examples include, for example, methoxymethoxy group, methoxypropoxy group, ethoxypropoxy group, heptyloxyethoxy group, and the like.
The "(C_1-6 alkoxy)(C_1-6 alkyl) group" means a group formed by binding the aforementioned C_1-6 alkoxy group and the aforementioned C_1-6 alkyl group, and examples include, for example, methoxymethyl group, methoxypropyl group, ethoxypropyl group, heptyloxyethyl group, and the like.

[0055] The "aryloxy group" is a group corresponding to the aforementioned "aryl group" substituting via oxygen atom, and examples include, for example, phenoxy group, naphthoxy group, and the like.
The "C_1-6 hydroxyalkyl group" means the aforementioned C_1-6 alkyl group substituted with 1 to 2 of hydroxyl groups, and examples include, for example, hydroxymethyl group, 2-hydroxyethyl group, 4-hydroxybutyl group, and the like.

[0056]  The "C_1-10 alkylthio group" is a linear or branched alkylthio group having 1 to 10 carbon atoms, and examples include, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, 2-butylthio group, t-butylthio group, 1,1-dimethylethylthio group, n-pentylthio group, isopentylthio group, 1,1-dimethylpropylthio group, n-hexylthio group, and the like.

[0057] The "C_1-10 haloalkylthio group" is an alkylthio group consisting of the aforementioned "C_1-10 alkylthio group" substituted with one or two or more halogen atoms, and examples include, for example, fluoromethylthio group, difluoromethylthio group, trifluoromethylthio group, 2,2,2-trifluoroethylthio group, 2,2,2-trichloroethylthio group, pentafluoroethylthio group, 4-fluorobutylthio group, 4-chlorobutylthio group, 4-bromobutylthio group, perfluorohexylthio group, and the like.

[0058] The "C_2-10 alkenylthio group" is a linear or branched alkenylthio group having 2 to 10 carbon atoms, and examples include, for example, vinylthio group, allylthio group, n-propenylthio group, isopropenylthio group, n-butenylthio group, 2-butenylthio group, n-pentenylthio group, n-hexenylthio group, and the like.
The "arylthio group" is a group corresponding to the aforementioned "aryl group" substituting via sulfur atom, and examples include, for example, phenylthio group, naphthylthio group, and the like.
The "C_2-6 alkenylthio group" is a linear or branched alkenylthio group having 2 to 6 carbon atoms, and examples include, for example, vinylthio group, 1-propenylthio group, 2-propenylthio group, 2-butenylthio group, 1,3-butadienylthio group, 2-pentenylthio group, 3-pentenylthio group, 2-hexenylthio group, and the like.

[0059] The "arylsulfonyl group which may be substituted with a halogen atom" is the aforementioned sulfonyl group of which aryl group may be substituted with one or two or more halogen atoms, and examples include, for example, phenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-fluorophenylsulfonyl group, 2,4-dibromophenylsulfonyl group, 2,4-difluorophenylsulfonyl group, naphthylsulfonyl group, 6-bromonaphthylsulfonyl group, and the like.

[0060] The "divalent C_1-10 aliphatic hydrocarbon group" means a C_1-10 alkylene group, a C_2-10 alkenylene group, a C_2-10 alkynylene group, a C_3-10 cycloalkylene group, or a C_3-10 cycloalkenylene group.
The "C_1-10 alkylene group" is a linear or branched alkylene group having 1 to 10 carbon atoms, and examples include, for example, -CH₂-, -(CH₂)₂ -, -(CH₂)₃ -, -CH(CH₃)-, -(CH₂)₃-, -(CH(CH₃))₂-, -(CH₂)₂-CH(CH₃)-, -(CH₂)₃-CH(CH₃)-, -(CH₂)₂ -CH(C₂H₅)-, -(CH₂)₆ -, -(CH₂)₂-C(C₂H₅)₂ -, -(CH₂)₃C(CH₃)₂CH₂-, -(CH₂)₈-, -(CH₂)₃C(CH₃)₂(CH₂)₃-, -(CH₂)₁₀-, and the like.

[0061] The "C_2-10 alkenylene group" is a linear or branched alkenylene group of 2 to 10 carbon atoms having one or two or more double bonds in the chain, and examples include, for example, a divalent group having a double bond formed by eliminating 2 to 6 hydrogen atoms on adjacent carbon atoms of the aforementioned alkylene group.

[0062] The "C_2-10 alkynylene group" is a linear or branched alkynylene group of 2 to 10 carbon atoms having one or two or more triple bonds in the chain, and examples include, for example, a divalent group having a triple bond formed by further eliminating hydrogen atoms from carbon atoms at the double bond moiety of the aforementioned alkenylene group.
Further, the "divalent C_1-10 aliphatic hydrocarbon group" may contain a double bond and triple bond.

[0063] The "C_3-10 cycloalkylene group" is a divalent group formed by eliminating arbitrary 2 of hydrogen atoms from a cycloalkane having 3 to 10 carbon, and examples include, for example, 1,2-cyclopentylene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group, 1,3-cycloheptylene group, and the like.

[0064] The "C_3-10 cycloalkenylene group" is a divalent group formed by eliminating arbitrary 2 of hydrogen atoms from a cycloalkene having 3 to 10 carbon atoms, and examples include, for example, 3-cyclohexen-1,2-ylene group, 2,5-cyclohexadien-1,4-ylene group, and the like.

[0065] The "arylene group" is a divalent group formed by eliminating arbitrary 2 of hydrogen atoms from a mono- to tetracyclic aromatic hydrocarbon having 6 to 18 carbon atoms, and examples include, for example, divalent groups formed by eliminating arbitrary 2 of hydrogen atoms from benzene, naphthalene, azulene, fluorene, phenanthrene, anthracene, pyrene, and the like.

[0066] The "divalent heterocyclic group" is a divalent group formed by further eliminating arbitrary 1 of hydrogen atom from the aforementioned "heterocyclic group", and examples include, for example, divalent groups formed by eliminating arbitrary 1 of hydrogen atom from pyrazolidinyl group, oxolanyl group, thiolanyl group, piperidinyl group, piperazinyl group, morpholinyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, quinolyl group, isoquinolyl group, thienyl group, pyrrolyl group, thiazolyl group, isothiazolyl group, pyrazolyl group, imidazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, benzofuranyl group, benzothienyl group, indolyl group, benzoxazolyl group, benzisoxazolyl group, indazolyl group, benzimidazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, indolidinyl group, and thienopyridyl group.

[0067] The "protected hydroxyl group" means hydroxyl group protected with "a protective group of hydroxyl group".
The "protected amino group" means amino group protected with "a protective group of amino group".
The "protected oxime group" means oxime group protected with "a protective group of oxime group".
Examples of the "protective group of hydroxyl group", "protective group of amino group" and "protective group of oxime group" include a silyl type protective group such as trimethylsilyl group, triethylsilyl group and tert-butyldimethylsilyl group, an acyl type protective group such as acetyl group and benzoyl group, an ether type protective group such as benzyl group, p-methoxybenzyl group and 2-chlorobenzyl group, a carbonate type protective group such as benzyloxycarbonyl group and tert-butyloxycarbonyl group, and the like.

[0068] The "cyclic amino group formed together with the adjacent nitrogen atom" in the definitions of R²² and R²³, or R²⁴ and R²⁵ is a 3 to 8-membered saturated cyclic amino group, one of which methylene group in the ring may be replaced with oxygen atom, or NH group, and examples include, for example, piperidinyl group, piperazinyl group, morpholino group, and the like.

[0069] The "C_3-10 cycloalkyl group condensed with an aryl group" is a group corresponding to the aforementioned C_3-10 cycloalkyl group condensed with the aforementioned aryl group, and examples include, for example, indanyl group, and the like.

[0070] In the present invention, a pharmaceutically acceptable salt means a salt used in chemotherapeutic and prophylactic treatment of bacterial infectious diseases. Examples include, for example, salts with an acid such as acetic acid, propionic acid, butyric acid, formic acid , trifluoroacetic acid, maleic acid, tartaric acid, citric acid, stearic acid, succinic acid, ethylsuccinic acid, lactobionic acid, gluconic acid, glucoheptonic acid, benzoic acid, methanesulfonic acid, ethanesulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid, laurylsulfuric acid, malic acid, aspartic acid, glutamic acid, adipic acid, cysteine, N-acetylcysteine, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, hydroiodic acid, nicotinic acid, oxalic acid, picric acid, thiocyanic acid, undecanoic acid, acrylic acid polymer, and carboxyvinyl polymer, salts with an inorganic base such as sodium salts, potassium salts and calcium salts, salts with an organic amine such as morpholine and piperidine, and salts with an amino acid.

[0071] The compounds of the present invention and pharmacologically acceptable salts thereof may exist in the form of an adduct with water or various kinds of solvents, and such an adduct or solvate also falls within the scope of the salt of the present invention. More specifically, a compound which is a solvate and is also a salt falls within the scope of the salt referred to in the present invention. Examples of the solvate include, for example, hydrate, and the like. Further, isomers of the compounds (1) may exist, and all possible isomers and mixtures thereof including the aforementioned isomers fall within the scope of the present invention. These isomers can be separated and purified according to known methods.

Effect of the present invention

[0072] The compounds of the present invention have broad antibacterial activities and are effective especially against Hemophilus influenzae, erythromycin resistant pneumococci, and the like.

Best Mode for Carrying Out the Invention

[0073] The compounds of the present invention can be synthesized by, for example, the following methods. However, it should be understood that the preparation methods of the compounds of the present invention are not limited to these methods.

[0074] Although all of the compounds of the present invention are novel compounds not having been described in literatures, they can be prepared by known methods described in literatures, or similar methods. Examples of such literatures include S.R. Sandler et al., Organic Functional Group Preparations, Academic Press Inc., New York and London, 1968; S.R. Wagner et al., Synthetic Organic Chemistry, John Wiley, 1961; R.C. Larock, Comprehensive Organic Transformations, 1989; L.A. Paquette et al., Encyclopedia of Reagents for Organic Synthesis, 1995; Compendium of Organic Synthetic Methods, and the like.

[0075] Examples of the preparation methods are shown below. In the text of the specification, the term base means, unless specifically indicated, an organic base (e.g., an amine such as triethylamine, diisopropylethylamine, pyridine and 4-dimethylaminopyridine, a metal alkoxide such as sodium methoxide, and the like), or an inorganic base (e.g., an alkali metal carbonate such as sodium carbonate and potassium carbonate, an alkaline earth metal carbonate such as calcium carbonate, a metal hydroxide such as sodium hydroxide and potassium hydroxide, and the like).

[0076] The term solvent means, unless specifically indicated, a polar solvent (e.g., water, an alcohol type solvent such as methanol, and the like), an inert solvent (e.g., a halogenated hydrocarbon type solvent such as chloroform and methylene chloride, an ether type solvent such as diethyl ether, tetrahydrofuran and 1,4-dioxane, an aprotic solvent such as dimethylformamide, dimethyl sulfoxide and acetonitrile, an aromatic hydrocarbon type solvent such as toluene, a hydrocarbon such as cyclohexane, and the like), or a mixed solvent thereof.

[0077] The condensing agent means, unless specifically indicated, for example, a chloroformic acid ester (e.g., isobutyl chloroformate, ethyl chloroformate, methyl chloroformate and the like), an acid chloride (e.g., pivaloyl chloride, oxalyl chloride, 2,4,6-trichlorobenzoyl chloride and the like), a dehydration condensing agent (e.g., a carbodiimide reagent such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and dicyclohexylcarbodiimide), carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide salt, and the like), and the like.

<Scheme 1>

[0078] 

[0079] (In the formula, R¹⁶ represents hydrogen atom, or hydroxyl group, and the other symbols have the same meanings as those defined above.)

[Step 1]

[0080] The erythromycin analogue compounds represented by the formula (1) can be synthesized by, for example, the methods described in the patent documents (WO99/28332, WO02/096922, U.S. Patent No. 6,420,535, WO01/077134, WO00/069875, WO05/030786, WO04/078770 and the like). The erythromycin analogue compounds represented by the formula (1) can also be obtained by reducing a compound wherein R⁵ and R⁶ combine together to form carbonyl group with a hydride reducing agent or the like, and then converting hydroxyl groups into other substituents defined as R⁵ and R⁶ according to a generally used functional group conversion method. As the aforementioned reducing agent, for example, sodium borohydride, and lithium triethylborohydride are preferred. The compounds represented by the formula (2) can be prepared according to the method described in WO03/014136 by using a compound represented by the formula (1) as a starting material. Specifically, the compounds represented by the formula (2) can be obtained by stirring a compound represented by the formula (1) at room temperature with an oxidizing agent (examples include, for example, lead tetraacetate, periodic acid salts and the like, and among them, lead tetraacetate is preferred) in a solvent (chloroform is especially preferred). As the compound represented by formula (1), a compound wherein R⁵ is
a protected hydroxyl group, and R⁶ is hydrogen atom is preferred. The compounds represented by the formula (2) can be used in the following step 2 without isolation from the reaction system.

[Step 2]

[0081] The compounds represented by the formula (3) can be obtained by stirring a compound represented by the formula (2) in a solvent in the presence of an oxidizing agent. Examples of the oxidizing agent for this reaction include, for example, sodium chlorite, sodium perchlorate, potassium permanganate, and the like, and among them, sodium chlorite is preferred. As the solvent, a mixed solvent of chloroform, tetrahydrofuran, tert-butyl alcohol and water are preferred. The reaction temperature is selected from the range of, for example, -20°C to the boiling temperature of the solvent, and a temperature of from 0°C to room temperature is especially preferred.

[Step 3]

[0082] The compounds represented by the formula (4) can be obtained by stirring a compound represented by the formula (3) in a condensing agent (a chloroformic acid ester is preferred) and a solvent (chloroform is preferred) in the presence or absence of an organic base (an amine such as triethylamine is preferred), then adding, for example, ammonia when R¹⁶ is hydrogen atom, or adding, for example, hydroxylamine when R¹⁶ is hydroxyl group, and stirring the mixture. Although ammonia is preferably added as ammonia gas, it may also be added as a solution in a solvent (for example, water, alcohol, dioxane and the like). Hydroxylamine can be used in a state of a solution in a solvent (examples of the solvent include, for example, water, alcohol, dioxane and the like, and water is especially preferred). The reaction temperature is selected from a range of, for example, -20°C to room temperature, and a temperature of from -5°C to 5°C is especially preferred.

[Step 4]

[0083] The compounds represented by the formula (5) can be obtained by stirring a compound represented by the formula (4) wherein R¹⁶ is hydrogen atom in a solvent (e.g., ethyl acetate and the like) in the presence of iodobenzene diacetate, iodobenzene bistrifluoroacetate or the like. Further, the compounds represented by the formula (5) can also be obtained by stirring a compound represented by the formula (4)
wherein R¹⁶ is hydroxyl group in a solvent (tetrahydrofuran is especially preferred) in the presence of a sulfonyl chloride (examples include, for example, p-toluenesulfonyl chloride, methanesulfonyl chloride and the like, and among them, p-toluenesulfonyl chloride is especially preferred). The compounds of the formula (5) can be used for the following step 5 without isolation from the reaction system.

[Step 5]

[0084] The compounds represented by the formula (6) can be obtained by stirring a compound represented by the formula (5) in an aqueous solution of a metal hydroxide (examples include, for example, lithium hydroxide, sodium hydroxide and the like, and among them, lithium hydroxide is preferred), or in a mixed solvent of such an aqueous solution and an alcohol solvent such as methanol and ethanol, tetrahydrofuran, or the like. The reaction temperature is selected from a range of, for example, from 0°C to the boiling temperature of the solvent, and a temperature of from 0°C to room temperature is especially preferred.

[Step 6]

[0085] In Step 6, it is preferable to use compounds represented by the formulas (9) to (11) for the reaction.

[0086] 

[0087] (In the formulas, X represents a leaving group (e.g., chloro group, bromo group, iodo group, methanesulfonyloxy group and the like), R⁷ represents a group defined for R⁷ other than hydrogen atom, and the other symbols have the same meanings as those defined above.)

[0088] The compounds represented by the formula (7) wherein R⁷ is hydrogen atom can be obtained by reacting a compound represented by the formula (6) with an epoxide represented by the formula (9) in a solvent (tetrahydrofuran is especially preferred) in the presence or absence of a Lewis acid (for example, ytterbium triflate) with heating, or by reacting a compound represented by the formula (6) with a compound represented by the formula (10) in an inert solvent in the presence of a base with heating.

[0089] The compounds represented by the formula (7) wherein R⁷ is other than hydrogen atom can be obtained by a method of stirring a compound represented by the formula (7) wherein R⁷ is hydrogen atom obtained by the aforementioned method, a corresponding aldehyde and a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like) in a solvent, or a method of reacting the compound with a compound represented by the formula (11) in an inert solvent in the presence of a base. The reaction temperature of the aforementioned reaction is selected from the range of, for example, 0°C to the boiling temperature of the solvent.

[Step 7]

[0090] By using a compound represented by the formula (7) wherein R⁷ is hydrogen atom as a starting material, and reacting it with a Mitsunobu reagent (for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate and the like) in an inert solvent (tetrahydrofuran is especially preferred) in the presence of a phosphine reagent (for example, triphenylphosphine and the like), the compounds represented by the formula (8) wherein R⁷ is hydrogen atom can be obtained. In this case, the reaction temperature is selected from the range of, for example, 0°C to room temperature, and room temperature is preferred.

[0091] By a method of reacting a compound represented by the formula (8) wherein R⁷ is hydrogen atom with a corresponding aldehyde and a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like) in a solvent, or a method of reacting the compound with a compound represented by the formula (11) in an inert solvent in the presence of a base, the compounds of the formula (8) wherein R⁷ is other than hydrogen atom can be obtained.

[0092] By reacting a reaction solution obtained by reacting a compound represented by the formula (7) wherein R⁷ is other than hydrogen atom in a condensing agent (2,4,6-trichlorobenzoyl chloride is preferred) and a solvent (tetrahydrofuran is preferred) in the presence of an organic base (an amine such as triethylamine is preferred) with a solution of a base (4-dimethylaminopyridine is preferred) in a solvent (acetonitrile is especially preferred), the compounds represented by the formula (8) wherein R⁷ is other than hydrogen atom can be obtained. The reaction temperature is selected from the range of, for example, 0°C to the boiling temperature of the solvent.

<Scheme 2>

[0093] 

(In the formulas, the symbols have the same meanings as those defined above.)

[0094] The compounds represented by the formula (7) mentioned in Scheme 1 can also be obtained by converting a compound represented by the formula (6) into a compound represented by the formula (12) by a method of stirring the compound represented by the formula (6) with a corresponding aldehyde and a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like) in a solvent, or a method of reacting it with a compound represented by the formula (11) in an inert solvent in the presence of a base, as shown in Scheme 2, and then reacting the converted compound with an epoxide represented by the formula (9) in a solvent (tetrahydrofuran is especially preferred) in the presence of a Lewis acid (for example, ytterbium triflate) with heating, or by reacting it with a compound represented by the formula (10) in an inert solvent in the presence of a base with heating.

<Scheme 3>

[0095] 

[0096] (In the formula, R^3' is:

a group represented by the formula -X⁰³¹-R⁰³¹,

a group represented by the formula -X^031'-A⁰³¹-X⁰³²-R⁰³¹,

a group represented by the formula -X^031'-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-R⁰³¹, or

a group represented by the formula -X^031'-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-A⁰³³-X⁰³⁴-R⁰³¹,
wherein X^031' is:

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-, or

a group represented by the formula -OCON(R²⁰)-,

A⁰³¹,X⁰³²,A⁰³²,X⁰³³,A⁰³³,X⁰³⁴ and R⁰³¹ have the same meanings as

those defined above, and
the other symbols in the formulas have the same meanings as those defined above.)

[0097] The compounds represented by the formula (14) wherein X^031' is a group of the formula -OCO- can be obtained by a method similar to the methods described in the patent documents (U.S. Patent No. 6,191,118, WO04/101584, WO05/030786 and the like). Specifically, the compounds represented by the formula (14) wherein X^031' is a group of the formula -OCO- can be obtained by a method of reacting a compound represented by the formula (13) in an inert solvent in the presence of a corresponding carboxylic acid and a condensing agent, or with a corresponding acid anhydride or a corresponding acid chloride in an inert solvent in the presence or absence of a base. The reaction temperature is selected from the range of, for example, 0°C to the boiling temperature of the solvent. Further, the compounds represented by the formula (14)
wherein X^031' is a group of the formula -OCON(R²⁰)- can be obtained by a method similar to the method described in U.S. Patent No. 5,523,399. Specifically, by a method of reacting a compound represented by the formula (13) and carbonyldiimidazole in an inert solvent at a temperature of 0°C to the boiling temperature of the solvent, and then adding a corresponding amine, or a method of reacting the same with triphosgene in an inert solvent in the presence of a base, and then adding a corresponding amine, or a method of reacting a compound represented by the formula (13) and a corresponding isocyanate in an inert solvent, a compound represented by the formula (14) wherein X^031' is a group of the formula -OCON(R²⁰)-can be obtained. Further, the compounds represented by the formula (14) wherein X^031' is a group of the formula -OCO₂- can be obtained by a method similar to the methods described in the patent documents WO93/013116, WO93/021200, WO93/021199 and the like. Specifically, by a method of reacting a compound represented by the formula (13) and triphosgene in an inert solvent in the presence of a base, and then reacting the resultant with a corresponding alcohol, a compound represented by the formula (14) wherein X^031' is a group of the formula -OCO₂- can be obtained. The reaction temperature is selected from the range of, for example, 0°C to the boiling temperature of the solvent.

[0098] Further, among the compounds represented by the formula (8) shown in Scheme 1, those compounds shown in Scheme 4 can also be obtained by the steps shown in Scheme 4, not only the steps shown in Scheme 1.

<Scheme 4>

[0099] 

[0100] (In the formulas, Y¹ is:

a group represented by the formula -X^061'-R⁰⁶¹,

a group represented by the formula -X^061'-A⁰⁶¹-X⁰⁶²-R⁰⁶¹,

a group represented by the formula -X^061'-A⁰⁶¹-X⁰⁶²-A⁰⁶² -X⁰⁶³-R⁰⁶¹, or

a group represented by the formula -X^061'-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-A⁰⁶³-X⁰⁶⁴-R⁰⁶¹,
wherein X^061' is:

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-, or

a group represented by the formula -OCON(R²⁰)-, and
A⁰⁶¹,X⁰⁶²,A⁰⁶²,X⁰⁶³,A⁰⁶³,X⁰⁶⁴,R⁰⁶¹ and R²⁰ have the same meanings as those defined above,

Y² is:

a group represented by the formula -X^061''-R⁰⁶¹,

a group represented by the formula -X^061''-A⁰⁶¹-X⁰⁶²-R⁰⁶¹,

a group represented by the formula -X^061''-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-R⁰⁶¹, or

a group represented by the formula -X^061''-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-A⁰⁶³-X⁰⁶⁴-R⁰⁶¹,
wherein X^061'' is:

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-, and

A⁰⁶¹,X⁰⁶²,A⁰⁶²,X⁰⁶³,A⁰⁶³,X⁰⁶⁴,R⁰⁶¹,R²⁰ and R²¹ have the same meanings as those defined above,

Y³ is:

a group represented by R⁰⁶²,

a group represented by the formula -A⁰⁶⁴-X⁰⁶⁶-R⁰⁶²,

a group represented by the formula -A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-R⁰⁶², or

a group represented by the formula -A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-A⁰⁶⁶-X⁰⁶⁸-R⁰⁶²,

A⁰⁶⁴,X⁰⁶⁶,A⁰⁶⁵,X⁰⁶⁷,A⁰⁶⁶,X⁰⁶⁸ and R⁰⁶² have the same meanings as those defined above, and
the other symbols have the same meanings as those defined above.)

[0101] The compounds represented by the formula (16) can be obtained by oxidizing a compound represented by the formula (15) by, for example, Swern oxidation, Corey-Kim Oxidation, or the like.

[0102] The compounds represented by the formula (17) can be obtained by reacting a compound represented by the formula (16) and a hydroxylamine salt such as hydroxylamine hydrochloride or hydroxylamine in a solvent (methanol is preferred) in the presence or absence of a base (imidazole is especially preferred).

[0103] The compounds represented by the formula (20) can be obtained by using a compound represented by the formula (16) as a starting material according to a method similar to the methods described in the literatures (Tetrahedron Letters, 1971, vol. 2, p.195; Tetrahedron Letters, 1972, vol. 1, p.29), specifically, by reacting the carbonyl group with hydrazine in a polar solvent to convert it into hydrazono group, and then reacting the resultant with sodium nitrite or the like, or by reacting it with hydroxylamine in a solvent to convert it into oxime group, then reacting the resultant with titanium chloride or the like to obtain an imino compound, and reducing the imino compound with a hydride reducing agent or the like.

[0104] The compounds represented by the formula (19) can be obtained by using a compound represented by the formula (17) as a starting material, and reacting it by a method similar to the method described in European Patent No. 284203 or WO93/13116 in the presence or absence of a crown ether (for example, 18-crown-6-ether and the like), specifically, reacting it with a corresponding alkyl halide or the like in an inert solvent in the presence or absence of a base.

[0105] The compounds represented by the formula (21) can be obtained by reacting a compound represented by the formula (20) and a corresponding acid chloride, a corresponding acid anhydride, a corresponding sulfonyl chloride, a corresponding isocyanate, a corresponding chloroformate or the like in an inert solvent in the presence or absence of a base.

[0106] The compounds represented by the formula (18) can be obtained by reacting a compound represented by the formula (15) and a corresponding alkyl halide, a corresponding acid chloride, a corresponding acid anhydride, a corresponding isocyanate, a corresponding chloroformate or the like in an inert solvent in the presence or absence of a base.

<Scheme 5>

[0107] 

[0108] (In the formulas, Y⁴ and Y^4' represent:

a group represented by R³³¹,

a group represented by the formula -A³³¹-X³³²-R³³¹,

a group represented by the formula -A³³¹-X³³²-A³³²-X³³³-R³³¹, or

a group represented by the formula -A³³¹-X³³²-A³³²-X³³³-A³³³-X³³⁴-R³³¹, A³³¹, X³³², A³³², X³³³, A³³³, X³³⁴ and R³³¹ have the same meanings as those defined above, and
the other symbols have the same meanings as those defined above.)

[0109] The compounds represented by the formula (23) can be obtained by using a compound represented by the formula (22) as a starting material, according to a method similar to the method described in European Patent No. 895999, specifically, by condensing it with a corresponding carboxylic acid by a generally used method.

[0110] Further, the compounds represented by the formula (25) can be obtained by using a compound represented by the formula (22) as a starting material according to a method similar to the method described in European Patent No. 895999, specifically, by reacting it with a corresponding amine, via an imidazocarbonyl compound represented by the formula (24).

<Scheme 6>

[0111] 

[0112] (In the formulas, Y⁵ is:

a group represented by the formula -X³³⁵-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-R³³², or

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-A³³⁶-X³³⁸-R³³², X³³⁵, A³³⁴, X³³⁶, A³³⁵, X³³⁷, A³³⁶, X^{33 8} and R³³² have the same meanings as those defined above, and
the other symbols have the same meanings as those defined above.)
The compounds represented by the formula (27) can be obtained via a compound represented by the formula (26) obtainable by oxidizing a compound represented by the formula (22) by, for example, Swern oxidation, Corey-Kim Oxidation or the like according to a method similar to the method described in Japanese Patent Unexamined Publication (KOHYO) No. 2000-514097, specifically, by reacting it with a corresponding Grignard reagent or the like by a method well known to those skilled in the art, or by reacting a corresponding amine or the like, via an epoxy compound represented by the formula (28).

<Scheme 7>

[0113] 

[0114] (In the formulas, the symbols have the same meanings as those defined above.)

[0115] The compounds represented by the formula (30) can be obtained by reacting a compound represented by the formula (29) according to a method similar to the method described in Japanese Patent Unexamined Publication (KOHYO) No. 2000-514097, specifically, by reacting it with a reagent of the formula R³³⁴-CN, R³³⁴-CO₂ H, R³³⁴-C=NH(OCH₃) or the like in a solvent in the presence of a base, acid or a Lewis acid at a temperature of from room temperature to the boiling temperature of the solvent.

<Scheme 8>

[0116] 

[0117] (In the formulas, the symbols have the same meanings as those defined above.)

[0118] The compounds represented by the formula (33) can be obtained by reacting a compound represented by the formula (31) according to a method similar to the method described in the literature (The Journal of Antibiotics, 1998, vol. 8, p. 1029), specifically, by oxidizing the compound, then treating the resultant with triphenylphosphine to convert into a compound represented by the formula (32), and then reacting the resultant according to a method similar to the method described in WO01/074792, specifically, reacting it with a corresponding Grignard reagent or the like.

<Scheme 9>

[0119] 

(In the formulas, the symbols have the same meanings as those defined above.)

[0120] The compounds represented by the formula (35) can be obtained by reacting a compound represented by the formula (34) with a chloroformic acid ester, triphosgene or the like in a solvent (chloroform is especially preferred) in the presence of a base (pyridine is preferred).

<Scheme 10>

[0121] 

(In the formula, the symbols have the same meanings as those defined above.)

[0122] The compounds represented by the formula (37) can be obtained by reacting a compound represented by the formula (36) with triphosgene or the like in an inert solvent (chloroform or dichloromethane is desirable) in the presence of a base (pyridine is desirable).

[0123]  <Scheme 11>

[0124] 

(In the formulas, R^1' represents a halogen atom, and the other symbols have the same meanings as those defined above.)

[0125] The compounds represented by the formula (39) can be obtained by reacting a compound represented by the formula (38) according to a method similar to the method described in WO00/069875, specifically, by reaction with a corresponding halogenating reagent or the like (for example, N-fluorobenzenesulfonimide and the like) in an inert solvent in the presence or absence of a base.

<Scheme 12>

[0126] 

[0127] (In the formulas, Y⁸ is:

a group represented by the formula -X¹³¹-R¹³¹,

a group represented by the formula -X¹³¹-A¹³¹-X¹³²-R¹³¹,

a group represented by the formula -X¹³¹-A¹³¹-X¹³²-A¹³²-X¹³³-R¹³¹, or

a protective group of amino group,

X¹³¹, A¹³¹, X¹³², A¹³², X¹³³ and R¹³¹ have the same meanings as those defined above, and
the other symbols have the same meanings as those defined above.)

[0128] The compounds represented by the formula (42) can be obtained by reacting a compound represented by the formula (40) according to a method similar to the method described in WO04/013153, specifically, by converting it into a demethylated compound represented by the formula (41), and then reacting the resultant with a corresponding reagent in an inert solvent in the presence or absence of a base.

<Scheme 13>

[0129] 

[0130] (In the formula, Y⁹ is:

a group represented by the formula -X^331'-R³³¹,

a group represented by the formula -X^331'-A³³¹-X³³²-R³³¹

a group represented by the formula -X^331'-A³³¹-X³³²-A³³²-X³³³-R³³¹

a group represented by the formula -X^331'-A³³¹-X³³²-A³³²-X³³³-A³³³-X³³⁴-R³³¹
wherein X^331' is:

a group represented by the formula -N(R²O)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-, and

A³³¹, X³³², A³³², X³³³, A³³³, X³³⁴ and R³³¹ have the same meanings as those defined above, and the other symbols have the same meanings as those defined above)

[0131] The compounds represented by the formula (43) can be obtained according to a method similar to the method described in European Patent No. 549040, specifically, by using a compound represented by the formula (26) as a starting material, and reducing imino group, that is produced in a solvent and in the presence of a corresponding ammonium salt in the presence or absence of an acid (for example, acetic acid and the like), with a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like).
The compounds wherein R²⁰ is hydrogen atom can also be obtained by reacting a compound represented by the formula (26) with hydroxylamine in a solvent to convert into an oxime compound, and then hydrogenating the resultant with a reducing agent such as platinum oxide or Raney nickel, or by reaction with titanium chloride or the like and reducing the resulting imino compound with a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like).

[0132] The compounds represented by the formula (44) wherein X^331' is a group of the formula -NH- can be obtained by a method of using a compound represented by the formula (43) as a starting material, and stirring with a corresponding aldehyde and a hydride reducing agent (for example, sodium triacetoxyborohydride, sodium cyanoborohydride and the like) in a solvent, or by reaction with a corresponding halide, sulfonyloxy compound or the like in an inert solvent (N,N'-dimethylformamide is preferred) in the presence of a base. The compounds represented by the formula (44) wherein X^331' is a group of the formula -N(R²⁰)- can also be obtained by a method of using a compound wherein X^331' mentioned above is a group of the formula -NH- as a starting material, and stirring with a corresponding aldehyde and a hydride reducing agent (e.g., sodium triacetoxyborohydride, sodium cyanoborohydride and the like) in a solvent. The compounds represented by the formula (44) wherein X^331' is a group of the formula -N(R²⁰)CO- can be obtained by a method of reacting a compound represented by the formula (44) in the presence of a corresponding carboxylic acid and a condensing agent, or with a corresponding acid anhydride or a corresponding an acid chloride in the presence or absence of a base, in an inert solvent. The compounds represented by the formula (44) wherein X^331' is a group of the formula -N(R²⁰)CO₂- can be obtained by using a compound represented by the formula (43) as a starting material, and reaction with a corresponding chloroformate reagent in an inert solvent. The compounds represented by the formula (44) wherein X^031' is a group of the formula -N(R²⁰)CON(R²¹)- can also be obtained by a method of using a compound represented by the formula (43) as a starting material, and reaction with N,N'-carbonyldiimidazole or triphosgene in an inert solvent (N,N'-dimethylformamide, tetrahydrofuran, chloroform or dichloromethane is preferred), and then reacting the resultant with a corresponding amine reagent in an inert solvent, or a method of reacting a compound represented by the formula (29) with a corresponding isocyanate reagent in an inert solvent. The compounds represented by the formula (44) wherein X^331' is a group of the formula -N(R²⁰)SO₂ - can be
obtained by using a compound represented by the formula (43) as a starting material, and reaction with a corresponding chlorosulfonyl reagent in an inert solvent (chloroform or dichloromethane is preferred) in the presence or absence of a base (triethylamine or pyridine is preferred).

[0133] Hydroxyl group, amino group, carboxyl group and oxime group contained in the compounds represented by the formulas (1) to (44) mentioned in these synthesis methods may be protected with selectively removable protective groups known in this field, and by removing them at a desired stage, the 10a-azalide compounds represented by the formula (I) and intermediates represented by the formula (II) for the synthesis of 10a-azalides can be provided. Examples of the known protective group include a silyl type protective group such as trimethylsilyl group, triethylsilyl group and tert-butyldimethylsilyl group, an acyl type protective group such as acetyl group and benzoyl group, an ether type protective group such as benzyl group, p-methoxybenzyl group and 2-chlorobenzyl group, a carbonate type protective group such as benzyloxycarbonyl group and tert-butyloxycarbonyl group, and the like. However, besides those mentioned above, protective groups described in Protective Groups in Organic Syntheses (Third Edition, 1999, Ed. by P.G.M. Wuts, T. Green), and the like can also be used. Further, the substituents of the compounds represented by the formulas (1) to (44) mentioned in these synthesis methods can be interchangeably converted by known methods.

[0134] The preparation methods of the compounds of the present invention are not limited by the aforementioned methods or the methods specifically described in the examples, and the substituents of the compounds of the present invention can be interchangeably converted by known methods using the compounds of the present invention as intermediates.

[0135] The intermediates and the objective compounds mentioned in the aforementioned preparation methods can be isolated and purified by purification methods commonly used in organic synthetic chemistry, for example, neutralization, filtration, extraction, washing, drying, concentration, recrystallization using a solvent such as ethyl acetate, ethyl acetate-hexane, isopropyl alcohol, ethanol, hydrated ethanol, acetone and hydrated acetone, various chromatography techniques, and the like. The intermediates can also be used in subsequent reactions without particular purification.

[0136] The compounds (I) and the compounds (II) include those of which isomers can exist, and all possible isomers including the above compounds and mixtures thereof fall within the scope of the present invention.

[0137] The compounds of the present invention and pharmaceutically acceptable salts thereof may exist in the forms of adducts with water or various kinds of solvents, and these adducts also fall within the scope of the salts of the present invention.

Examples

[0138] The present invention will be further explained in detail with reference to reference examples, examples and test example.

Reference Example 1: Synthesis of benzyl(oxiran-2-ylmethyl)carbamic acid

[0139] N-Benzyloxycarbonyl-3-amino-1,2-propanediol (5 g) obtained by the method described in the patent document (WO02/072068) was dissolved in pyridine (20 ml), and the solution was added with p-toluenesulfonyl chloride (4.66 g). The mixture was stirred at room temperature for 3 hours, and then further added with p-toluenesulfonyl chloride (2.3 g), and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was added with 2 N hydrochloric acid and ethyl acetate, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in methanol (100 ml). The solution was added with potassium carbonate (8.32 g), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain the title compound (4.35 g).
MS (ESI) m/z = 230.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.60 (dd, J=4.66, 2.64Hz, 1H), 2.79 (t, J=4.35Hz, 1H), 3.07-3.16 (m, 1H), 3.22-3.34 (m, 1H), 3.57-3.69 (m, 1H), 4.93 (s, 1H), 5.12 (s, 2H), 7.27-7.46 (m, 5H)

Reference Example 2: Synthesis of 2-(3-bromophenyl)-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0140] 

(1) 4-Bromo-1-butene (25 g) was dissolved in dimethyl sulfoxide (160 ml), the solution was added with sodium azide (18.1 g), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with distilled water and diethyl ether, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under ordinary pressure to obtain 4-azido-1-butene (8.43 g).

[0141] 

(2) The compound obtained in (1) mentioned above (1.00 g) was dissolved in tetrahydrofuran (20 ml), the solution was added with triphenylphosphine (2.94 g), and the mixture was stirred at room temperature for 45 minutes. The mixture was added with distilled water (0.93 ml), and the mixture was stirred for 18 hours. Then, the mixture was added with 3-bromophenylacetic acid (2.77 g), 1-hydroxybenzotriazole (1.98 g), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.55 g) under ice cooling, and the mixture was stirred at room temperature for 18 hours.
The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1 to 1:1) to obtain an amide compound (1.90 g).

[0142] 

(3) Potassium hexacyanoferrate(III) (57.1 g), potassium carbonate (24.0 g), hydroquinidine 1,4-phthalazinediyl diether (450 mg), and potassium osmate(VI) dihydrate (42.6 mg) were dissolved in a mixed solvent of t-butyl alcohol (270 ml) and distilled water (300 ml), and the solution was added with a solution of the compound obtained in (2) mentioned above (15.5 g) in t-butyl alcohol (30 ml) under ice cooling. The mixture was stirred for 4 hours under ice cooling, and then added with sodium hydrogensulfite until foaming ceased. The mixture was added with chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform to chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a diol compound (17.6 g).

[0143] 

(4) By using the compound obtained in (3) mentioned above (17.5 g) as a starting material, the title compound (8.43 g) was obtained in the same manner as that of Reference Example 1.
MS (ESI) m/z = 306.1 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.42-1.58 (m, 1H), 1.86-1.97 (m, 1H), 2.36-2.49 (m, 1H), 2.67-2.76 (m, 1H), 2.86-2.95 (m, 1H), 3.39 (q, J=6.11Hz, 2H), 3.49 (s, 2H), 5.80-5.95 (m, 1H), 7.07-7.44 (m, 4H)

Reference Example 3: Synthesis of 2-(3-bromophenyl)-N-[2-(2-oxiran-2-yl)ethyl]acetamide

[0144] 

(1) 4-Azidobutane-1,2-diol (2.0 g) obtained by the method described in the literature (Heterocycles, 2003, vol. 61, p.481) was dissolved in methanol (10 ml), and the solution was added with 5% palladium-carbon (0.4 g) and 2 N hydrochloric acid (2 ml), and the mixture was stirred under hydrogen atmosphere of 1 atm, and at room temperature for 4 hours. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure to obtain 4-aminobutane-1,2-diol hydrochloride (1.8 g).

[0145] 

(2) 3-Bromophenylacetic acid (3.05 g) was dissolved in chloroform (30 ml), the solution was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.72 g) under ice cooling, and the mixture was stirred at same temperature for 30 minutes. The reaction mixture was added dropwise with a solution of the compound obtained in (1) mentioned above (1.67 g) in methanol (10 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain an amide compound (2.58 g).

[0146] 

(3) By using the compound obtained in (2) mentioned above (2.48 g) as a starting material, the title compound (0.97 g) was obtained in the same manner as that of Reference Example 1.
¹H-NMR (300MHz, CDCl₃) δ (ppm): 1.45-1.58 (m, 1H), 1.90-2.02 (m, 1H), 2.46 (dd, J=4.74, 2.56Hz, 1H), 2.71-2.76 (m, 1H), 2.89-2.97 (m, 1H), 3.41 (q, J=6.22Hz, 2H), 3.52 (s, 2H), 5.79 (s, 1H), 7.19-7.25 (m, 2H), 7.38-7.49 (m, 2H)

Reference Example 4: Synthesis of (2R)-4-aminobutane-1,2-diol

[0147] (2R)-4-Azidobutane-1,2-diol (12 g) obtained by the method described in the literature (Heterocycles, 2003, vol. 61, p.481) was dissolved in methanol (60 ml), the solution was added with 5% palladium-carbon (2.4 g), and the mixture was stirred at room temperature for 7 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (60 ml), the solution was added with 5% palladium-carbon (2.4 g), and the mixture was stirred at room temperature for 1.5 days under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain the title compound (9.56 g).
MS (ESI) m/z = 105.9 [M+H]^+
1H-NMR (300MHz, CD₃OD) δ (ppm): 1.52-1.68 (m, 1H), 1.67-1.83 (m, 1H), 2.79-3.00 (m, 2H), 3.27-3.34 (m, 1H), 3.42-3.53 (m, 1H), 3.63-3.75 (m, 1H)

Reference Example 5: Synthesis of 2-(2-bromophenyl)-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0148] By using the compound obtained in Reference Example 4 (3.45 g) and 2-bromophenylacetic acid (8.46 g) as starting materials, the title compound (2.20 g) was obtained in the same manners as those of Reference Example 3, (2) and Reference Example 1.
MS (ESI) m/z = 306.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.47-1.62 (m, 1H), 1.86-1.99 (m, 1H), 2.44 (dd, J=4.82, 2.64Hz, 1H), 2.71 (dd, J=4.66, 4.20Hz, 1H), 2.88-2.97 (m, 1H), 3.34-3.48 (m, 2H), 3.71 (s, 2H), 5.75 (s, 1H), 7.13-7.22 (m, 1H), 7.28-7.39 (m, 2H), 7.57-7.63 (m, 1H)

Reference Example 6: Synthesis of 2-(4-bromophenyl)-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0149] By using the compound obtained in Reference Example 4 (3.25 g) and 4-bromophenylacetic acid (7.31 g) as starting materials, the title compound (2.24 g) was obtained in the same manners as those of Reference Example 3, (2) and Reference Example 1.
MS (ESI) m/z = 306.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.42-1.56 (m, 1H), 1.89-2.03 (m, 1H), 2.45 (dd, J=4.82, 2.64Hz, 1H), 2.70-2.76 (m, 1H), 2.88-2.97 (m, 1H), 3.40 (q, J=6.22Hz, 2H), 3.50 (s, 2H), 5.66-5.86 (m, 1H), 7.12-7.19 (m, 2H), 7.44-7.51 (m, 2H)

Reference Example 7: Synthesis of 2-(3-bromophenyl)-N-methyl-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0150] 

(1) 4-Bromo-1-butene (6.65 g) was dissolved in dimethylformamide (50 ml), the solution was added with N-methylbenzylamine (5.97 g), and the mixture was stirred at 60°C for 2 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was washed successively with distilled water and brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain a coupling compound (2.54 g).

[0151] 

(2) AD-mix-β(19.97 g) was dissolved in a mixed solvent of t-butyl alcohol (70 ml) and distilled water (70 ml), and the solution was added with the compound obtained in (1) mentioned above (2.50 g) under ice cooling. The mixture was stirred for 6 hours under ice cooling, and then added with sodium hydrogensulfite until foaming ceased. The mixture was added with chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a diol compound (2.45 g).

[0152] 

(3) The compound obtained in (2) mentioned above (2.40 g) was dissolved in methanol, the solution was added with 20% palladium hydroxide-carbon (1 g), and the mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure to obtain an amine compound (1.49 g).

[0153] 

(4) 3-Bromophenylacetic acid (3.23 g) was dissolved in chloroform (30 ml), the solution was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.88 g) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with a solution of the compound obtained in (3) mentioned above (1.49 g) in methanol (10 ml), and the mixture was stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain an amide compound (843 mg).

[0154] 

(5) By using the compound obtained in (4) mentioned above (843 mg) as a starting material, the title compound (393 mg) was obtained in the same manner as that of Reference Example 1.
MS (ESI) m/z = 298.0 [M+H]⁺

Reference Example 8: Synthesis of 2-(3-bromophenyl)-N-[(2R)-oxiran-2-ylmethyl]acetamide

[0155] 

(1) By using 3-bromophenylacetic acid (10 g) and allylamine (4.18 ml) as starting materials, an amide compound (10.58 g) was obtained in the same manner as that of Reference Example 3, (2).

[0156] 

(2) By using the compound obtained in (1) mentioned above (5 g) as a starting material, a diol compound (6.48 g) was obtained in the same manner as that of Reference Example 7, (2).

[0157] 

(3) By using the compound obtained in (2) mentioned above (6.3 g) as a starting material, the title compound (1.73 g) was obtained in the same manner as that of Reference Example 1.
MS (ESI) m/z = 292.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.51 (dd, J=4.59, 2.56Hz, 1H), 2.74-2.79 (m, 1H), 3.05-3.12 (m, 1H), 3.21-3.33 (m, 1H), 3.54 (s, 2H), 3.68-3.78 (m, 1H), 5.53-5.68 (m, 1H), 7.18-7.25 (m, 2H), 7.40-7.47 (m, 2H)

Reference Example 9: Synthesis of 2-(3-bromophenyl)-N-{3-[(2R)-oxiran-2-yl]propyl}acetamide

[0158] 

(1) 5-Bromo-1-pentene (6.65 g) was dissolved in dimethylformamide (50 ml), the solution was added with potassium phthalimide (13.7 g) under ice cooling, and the mixture was stirred at 60°C for 2 hours. The deposited solid was separated by filtration, and the filtrate was added with diethyl ether. Then, the mixture was washed successively with distilled water and saturated brine, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a phthalimide compound (15.7 g).

[0159] 

(2) The compound obtained in (1) mentioned above (15.7 g) was dissolved in ethanol (100 ml), the solution was added with hydrazine monohydrate (7.7 ml) under ice cooling, and the mixture was stirred at 60°C for 20 minutes. The reaction mixture was added with diluted hydrochloric acid under ice cooling to make the mixture acidic, and the deposited solid was separated by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was added with potassium hydroxide under ice cooling to make the residue basic, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an amine compound (5.14 g).

[0160] 

(3) By using the compound obtained in (2) mentioned above (2.5 g) as a starting material, the title compound (1.39 g) was obtained in the same manners as those of Reference Example 3, (2), Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 298.0 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.26-1.39 (m, 1H), 1.55-1.77 (m, 3H), 2.44 (dd, J=4.90, 2.72Hz, 1H), 2.75 (dd, J=4.82, 4.04Hz, 1H), 2.83-2.91 (m, 1H), 3.29 (q, J=6.63Hz, 2H), 3.51 (s, 2H), 5.71 (br.s.,1H), 7.18-7.24 (m, 2H), 7.39-7.46 (m, 2H)

Reference Example 10: Synthesis of N-(3-bromobenzyl)-3-[(2R)-oxiran-2-yl]propanamide

[0161] 

(1) 4-Pentenoic acid (2.96 g) was added with thionyl chloride (1.96 ml), and the mixture was stirred at 70°C for 2 hours. The reaction mixture was added with a solution of 3-bromobenzylamine (5.0 g) and triethylamine (11.2 ml) in chloroform (50 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated brine, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 5:1) to obtain an amide compound (2.01 g).

[0162] 

(2) By using the compound obtained in (1) mentioned above (2.01 g) as a starting material, the title compound (1.36 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 284.0 [M+H]⁺

Reference Example 11: Synthesis of 3-(3-bromophenyl)-N-[(2R)-oxiran-2-ylmethyl]propanamide

[0163] By using 3-(3-bromophenyl)propionic acid (2.5 g) and allylamine 0.80 ml) as starting materials, the title compound (1.01 g) was obtained in the same manners as those of Reference Example 3, (2) Reference Example 7, (2) and Reference Example 1. MS (ESI) m/z = 306.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.41-2.52 (m, 3H), 2.75 (t, J=4.27Hz, 1H), 2.95 (t, J=7.54Hz, 2H), 3.02-3.10 (m, 1H), 3.24-3.37 (m, 1H), 3.63-3.75 (m, 1H), 5.54 (s, 1H), 7.09-7.20 (m, 2H), 7.30-7.40 (m, 2H)

Reference Example 12: Synthesis of N-(3-bromophenyl)-4-[(2R)-oxiran-2-yl]butanamide

[0164] By using 5-hexenoic acid (3.65 g) and 3-bromoaniline (5.0 g) as starting materials, the title compound (690 mg) was obtained in the same manners as those of Reference Example 10, (1), Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 284.0 [M+H]⁺

Reference Example 13: Synthesis of 2-(1-naphthyl)-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0165] By using the compound obtained in Reference Example 4 (1.24 g) and 1-naphthylacetic acid (2.64 g) as starting materials, the title compound (0.51 g) was obtained in the same manners as those of Reference Example 3, (2) and Reference Example 1.
MS (ESI) m/z = 256.1 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.35-1.50 (m, 1H), 1.65-1.80 (m, 1H), 2.18 (dd, J=4.82, 2.64Hz, 1H), 2.42-2.47 (m, 1H), 2.49-2.55 (m, 1H), 2.66-2.76 (m, 1H), 3.20-3.40 (m, 1H), 4.03 (s, 2H), 5.57 (s, 1H), 7.27-7.61 (m, 4H), 7.79-8.00 (m, 3H)

Reference Example 14: Synthesis of 2-(5-bromopyridin-3-yl)-N-{2-[(2R)-oxiran-2-yl]ethyl}acetamide

[0166] By using the compound obtained in Reference Example 4 (1.29 g) and 5-bromo-3-pyridylacetic acid (2.21 g) as starting materials, the title compound (0.45 g) was obtained in the same manners as those of Reference Example 3, (2) and Reference Example 1.
MS (ESI) m/z = 307.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.43-1.57 (m, 1H), 2.01-2.13 (m, 1H), 2.51 (dd, J=4.66, 2.80Hz, 1H), 2.75-2.79 (m, 1H), 2.95-3.02 (m, 1H), 3.41-3.49 (m, 2H), 3.50 (s, 2H), 5.94 (s, 1H), 7.85 (t, J=2.10Hz, 1H), 8.44 (d, J=1.87Hz, 1H), 8.60 (d, J=2.18Hz, 1H)

Reference Example 15: Synthesis of 3-bromo-N-{3-[(2R)-oxiran-2-yl]propyl}benzamide

[0167] 

(1) The compound obtained in Reference Example 9, (2) (5.08 g) was dissolved in chloroform (50 ml), the solution was added with 3-bromobenzoic acid (7 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.01 g), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated aqueous ammonium chloride and chloroform, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 30:1) to obtain an amide compound (6.95 g).

[0168] 

(2) By using the compound obtained in (1) mentioned above (3 g) as a starting material, the title compound (2.54 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 306.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.38-1.53 (m, 1H), 1.69-1.97 (m, 3H), 2.56 (dd, J=4.82, 2.80Hz, 1H), 2.80-2.86 (m, 1H), 2.94-3.03 (m, 1H), 3.41-3.65 (m, 2H), 6.50 (s, 1H), 7.31 (t, J=7.93Hz, 1H), 7.60-7.65 (m, 1H), 7.68-7.73 (m, 1H), 7.94 (t, J=1.87Hz, 1H)

Reference Example 16: Synthesis of 2-(3-bromophenyl)furan

[0169] 1,3-Dibromobenzene (1.0 g) was dissolved in toluene (20 ml), the solution was added with tri-n-butyl-(2-furyl)tin 1.59 g) and tetrakistriphenylphosphine palladium (0.25 g), and the mixture was stirred for 30 minutes under reflux by heating. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in hexane. The solution was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in diethyl ether, the solution was added with cesium fluoride (1.01 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with a mixed solvent of hexane:ethyl acetate = 10:1, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane alone) to obtain the title compound (0.59 g).
MS (TOF) m/z = 222.0[M]^+
1H-NMR (300MHz, CDCl₃) δ (ppm):6.48 (dd, J=3.42, 1.71Hz, 1H), 6.67 (dd, J=3.42, 0.62Hz, 1H), 7.24 (t, J=7.85Hz, 1H), 7.35-7.41 (m, 1H), 7.48 (dd, J=1.79, 0.70Hz, 1H), 7.55-7.62 (m, 1H), 7.82 (t, J=1.79Hz, 1H)

Reference Example 17: Synthesis of 3-bromo-N-{5-[(2R)-oxiran-2-yl]pentyl}benzamide

[0170] 

(1) By using 7-bromo-1-heptene (5 g) as a starting material, an amine compound (2.87 g) was obtained in the same manners as those of Reference Example 9, (1) and (2).

[0171] 

(2) By using the compound obtained in (1) mentioned above (1.50 g) and 3-bromobenzoic acid (4.01 g) as starting materials, the title compound (1.55 g) was obtained in the same manners as those of Reference Example 3, (2), Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 312.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.32-1.74 (m, 8H), 2.47 (dd, J=5.05, 2.86Hz, 1H), 2.71-2.80 (m, 1H), 2.84-2.98 (m, 1H), 3.37-3.51 (m, 2H), 6.24-6.43 (m, 1H), 7.24-7.37 (m, 1H), 7.55-7.76 (m, 2H), 7.86-7.96 (m, 1H)

Reference Example 18: Synthesis of 3-bromo-N-[(2R)-oxiran-2-ylmethyl]benzamide

[0172] By using 3-bromobenzoic acid (5 g) and allylamine (1.86 ml) as starting materials, the title compound (0.75 g) was obtained in the same manners as those of Reference Example 3, (2), Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 277.9 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.66 (dd, J=4.43, 2.88Hz, 1H), 2.83-2.88 (m, 1H), 3.19-3.27 (m, 1H), 3.45-3.59 (m, 1H), 3.90-4.00 (m, 1H), 6.23-6.36 (m, 1H), 7.31-7.38 (m, 1H), 7.58-7.71 (m, 2H), 7.91-7.97 (m, 1H)

Reference Example 19: Synthesis of 3-bromo-N-{2-[(2R)-oxiran-2-yl]ethyl}benzamide

[0173] By using the compound obtained in Reference Example 4 (1.40 g) and 3-bromobenzoic acid (2.94 g) as starting materials, the title compound (0.61 g) was obtained in the same manners as those of Reference Example 3, (2) and Reference Example 1.
MS (ESI) m/z = 291.9 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.56-1.71 (m, 1H), 2.14-2.27 (m, 1H), 2.61 (dd, J=4.74, 2.72Hz, 1H), 2.81-2.87 (m, 1H), 3.06-3.14 (m, 1H), 3.60-3.69 (m, 2H), 6.61 (s, 1H), 7.31 (t, J=7.93Hz, 1H), 7.60-7.65 (m, 1H), 7.67-7.72 (m, 1H), 7.94 (t, J=1.79Hz, 1H)

Reference Example 20: Synthesis of N-(3-bromophenyl)-N'-{3-[(2R)-oxiran-2-yl]propyl}urea

[0174] 

(1) The compound obtained in Reference Example 9, (2) (0.37 g) was dissolved in tetrahydrofuran (3 ml), the solution was added with triethylamine (0.42 ml) and 3-bromophenyl isocyanate (0.315 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with distilled water and chloroform, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 30:1) to obtain an urea compound (0.95 g).

[0175] 

(2) By using the compound obtained in (1) mentioned above (0.9 g) as a starting material, the title compound (0.33 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 321.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.33-1.52 (m, 1H), 1.60-1.92 (m, 3H), 2.52 (dd,
J=4.83, 2.64Hz, 1H), 2.80 (t, J=4.40Hz, 1H), 2.87-3.03 (m, 1H), 3.25-3.40 (m, 2H), 4.96 (s, 1H), 6.48 (s, 1H), 7.06-7.30 (m, 3H), 7.53-7.60 (m, 1H)

Reference Example 21: Synthesis of 2-(3-azidopropyl)oxirane

[0176] 

(1) 4-Penten-1-ol (20.0 g) was dissolved in pyridine, the solution was added with p-toluenesulfonyl chloride (48.7 g) under ice cooling, and the mixture was stirred for 2 hours. The reaction mixture was added with hexane and distilled water, the layers were separated, and the organic layer was washed 4 times with 1 N hydrochloric acid, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a tosyl compound (54.1 g).

[0177] 

(2) The compound obtained in (1) mentioned above (54.0 g) was dissolved in dimethyl sulfoxide (500 ml), the solution was added with sodium azide (14.6 g), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with pentane, the layers were separated, and then the organic layer was concentrated under ordinary pressure to obtain an azide compound (11.8 g).

[0178] 

(3) The compound obtained in (2) mentioned above (20.7 g) was dissolved in dichloromethane (250 ml), and the solution was added portionwise with m-chloroperbenzoic acid (28.2 g) under ice cooling. The mixture was stirred at room temperature for 18 hours, and then filtered, the filtrate was successively washed with 10% aqueous sodium hydroxide and saturated aqueous sodium thiosulfate, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under ordinary pressure to obtain the title compound (23.7 g).
MS (ESI) m/z = 150.9 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.66 (m, 4H), 2.50 (dd, J=4.83, 2.64Hz, 1H), 2.73-2.81 (m, 1H), 2.89-2.97 (m, 1H), 3.36 (t, J=6.15Hz, 2H)

Reference Example 22: Synthesis of 2-(5-bromopentyl)oxirane

[0179] 7-Bromo-1-heptene (5.10 g) was dissolved in chloroform (29 ml), the solution was added with m-chloroperbenzoic acid (6.21 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with diethyl ether and saturated aqueous sodium thiosulfate, the layers were separated, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under ordinary pressure to obtain the title compound (5.27 g).
MS (TOF) = 193.0 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.36-1.63 (m, 6H), 1.82-1.91 (m, 2H), 2.46 (dd, J=5.04, 2.75Hz, 1H), 2.74 (dd, J=5.04, 3.67Hz, 1H), 2.87-2.93 (m, 1H), 3.40 (t, J=6.88Hz, 2H)

Reference Example 23: Synthesis of 3-bromo-N-{4-[(2R)-oxiran-2-yl]butyl}benzamide

[0180] 

(1) By using 6-bromo-1-hexene (5 g) as a starting material, an amine compound (3.16 g) was obtained in the same manners as those of Reference Example 9, (1) and (2).

[0181] 

(2) By using the compound obtained in (1) mentioned above (3.16 g) and 3-bromobenzoic acid (5.5 g) as starting materials, the title compound (2.58 g) was obtained in the same manners as those of Reference Example 3, (2), Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 298.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.48-1.80 (m, 6H), 2.48 (dd, J=5.05, 2.86Hz, 1H), 2.76 (dd, J=5.05, 4.18Hz, 1H), 2.85-2.99 (m, 1H), 3.30-3.55 (m, 2H), 6.32-6.55 (m, 1H), 7.22-7.38 (m, 1H), 7.56-7.76 (m, 2H), 7.86-7.99 (m, 1H)

Reference Example 24: Synthesis of N-{3-[(2R)-oxiran-2-yl]propyl}-1-naphthamide

[0182] 

(1) The compound obtained in Reference Example 9, (2) (1.0 g) was dissolved in chloroform (10 ml), the solution was added with triethylamine (4.9 ml) and 1-naphthyl chloride (1.8 ml) under ice cooling, and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with chloroform. The organic layer was washed with 0.5 N hydrochloric acid, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain an amide compound (2.27 g).

[0183] 

(2) By using the compound obtained in (1) mentioned above (2.04 g) as a starting material, the title compound (1.06 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 256.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.45-1.94 (m, 4H), 2.50 (dd, J=5.05, 2.86Hz, 1H), 2.74-2.81 (m, 1H), 2.89-3.03 (m, 1H), 3.58 (q, J=6.59Hz, 2H), 6.15-6.36 (m, 1H), 7.35-7.61 (m, 4H), 7.79-7.97 (m, 2H), 8.19-8.36 (m, 1H)

Reference Example 25: Synthesis of methyl 4-[(2R)-oxiran-2-yl]butanoate

[0184] 

(1) 5-Hexenoic acid (6.5 g) was dissolved in toluene (65 ml), the solution was added with p-toluenesulfonic acid monohydrate (490 mg) and benzyl alcohol (30 ml) under ice cooling, and the mixture was stirred for 3.5 hours under reflux by heating. The reaction mixture was left to cool, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 30:1 to 20:1) to obtain an ester compound (13.7 g).

[0185] 

(2) By using the compound obtained in (1) mentioned above (11.2 g) as a starting material, the title compound (7.04 g) was obtained in the same manners as those of Reference Example 2, (3) and Reference Example 1.
MS (ESI) m/z = 167.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.40-1.90 (m, 4H), 2.25-2.96 (m, 5H), 3.66 (s, 3H)

Reference Example 26: Synthesis of benzyl oxiran-2-ylacetate

[0186] 

(1) By using vinylacetic acid (15 g) as a starting material, an ester compound (42.4 g) was obtained in the same manner as that of Reference Example 25, (1).

[0187] 

(2) The compound obtained in (1) mentioned above (22.1 g) was dissolved in chloroform (90 ml), the solution was added with m-chloroperbenzoic acid (19.6 g) under ice cooling, and the mixture was stirred at room temperature for 48 hours.
The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, and saturated aqueous sodium thiosulfate, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1 to 5:1) to obtain the title compound (10.7 g).
MS (ESI) m/z = 215.0 [M+Na]^+
1H-NMR, (600MHz, CDCl₃) δ (ppm): 2.56 (dd, J=4.81, 2.52Hz, 1H), 2.61 (t, J=5.50Hz, 2H), 2.80-2.86 (m, 1H), 3.26-3.36 (m, 1H), 5.16 (s, 2H), 7.29-7.46 (m, 5H)

Reference Example 27: Synthesis of benzyl 5-oxiran-2-ylpentanoate

[0188] 

(1) By using 6-heptenoic acid (5.18 g) as a starting material, an ester compound (9.67 g) was obtained in the same manner as that of Reference Example 25, (1).

[0189] 

(2) By using the compound obtained in (1) mentioned above (4.72 g) as a starting material, the title compound (4.56 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 257.1 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.39-1.60 (m, 4H), 1.66-1.75 (m, 2H), 2.37 (t, J=7.57Hz, 2H), 2.44 (dd, J=5.04, 2.75Hz, 1H), 2.72-2.74 (m, 1H), 2.85-2.91 (m, 1H), 5.11 (s, 2H), 7.28-7.41 (m, 5H)

Reference Example 28: Synthesis of oxiran-2-ylmethyl (3-bromobenzyl)carbamate

[0190] 

(1) 3-Bromobenzylamine (1 g) was dissolved in chloroform (30 ml), the solution was added with allyl chloroformate (0.57 ml) and triethylamine (3.75 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 20:1) to obtain a carbamate compound (0.65 g).

[0191] 

(2) By using the compound obtained in (1) mentioned above (0.64 g) as a starting material, the title compound (0.43 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 308.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.60-2.71 (m, 1H), 2.85 (t, J=4.61Hz, 1H), 3.17-3.29 (m, 1H), 3.93 (dd, J=12.31, 6.59Hz, 1H), 4.36 (d, J=6.15Hz, 2H), 4.48 (dd, J=12.09, 2.86Hz, 1H), 5.12 (s, 1H), 7.17-7.25 (m, 2H), 7.32-7.49 (m, 2H)

Reference Example 29: Synthesis of 3-bromobenzyl (oxiran-2-ylmethyl)carbamate

[0192] 

(1) Allyl isocyanate (0.78 ml) was dissolved in toluene (10 ml), the solution was added with 3-bromobenzyl alcohol (1.5 g), and the mixture was stirred for 9 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 50:1) to obtain a carbamate compound (1.66 g).

[0193] 

(2) By using the compound obtained in (1) mentioned above (0.65 g) as a starting material, the title compound (0.55 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 308.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.60 (dd, J=4.40, 2.64Hz, 1H), 2.74-2.85 (m, 1H), 3.05-3.17 (m, 1H), 3.18-3.39 (m, 1H), 3.55-3.73 (m, 1H), 4.96 (s, 1H), 5.08 (s, 2H), 7.15-7.35 (m, 2H), 7.39-7.55 (m, 2H)

Reference Example 30: Synthesis of allyl (oxiran-2-ylmethyl)carbamate

[0194] 

(1) 3-Amino-1,2-propanediol (5 g) was dissolved in distilled water (280 ml), and the solution was added dropwise with allyl chloroformate (6.4 ml) under ice cooling. The mixture was further added dropwise with 0.4 N aqueous sodium hydroxide (140 ml). After the addition, the reaction mixture was stirred at room temperature for 36 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with 3 N hydrochloric acid to make the residue acidic, the mixture was extracted successively with chloroform and ethyl acetate, and then the organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a carbamate compound (3.40 g).

[0195] 

(2) By using the compound obtained in (1) mentioned above (3.0 g) as a starting material, the title compound (1.72 g) was obtained in the same manner as that of Reference Example 1.
MS (ESI) m/z = 180.0 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 2.56-2.65 (m, 1H), 2.75-2.82 (m, 1H), 3.06-3.13 (m, 1H), 3.40-3.51 (m, 1H), 3.56-3.66 (m, 1H), 4.06-4.10 (m, 2H), 5.18-5.24 (m, 2H), 5.85-5.97 (m, 1H)

Reference Example 31: Synthesis of (2R)-2-[4-(benzyloxy)butyl]oxirane

[0196] 

(1) 5-Hexen-1-ol (25.08 g) was dissolved in dimethylformamide (250 ml), and the solution was slowly added with sodium hydride (7.22 g) on an ice bath, and after foaming ceased, the mixture was added dropwise with a solution of benzyl alcohol (38.04 g) in dimethylformamide (30 ml). After the addition, the reaction mixture was warmed to room temperature, and stirred for 3 hours. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 20:1) to obtain a benzyl ether compound (48.33 g).

[0197] 

(2) By using the compound obtained in (1) mentioned above as a starting material, the title compound (8.00 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 229.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.43-1.81 (m, 6H), 2.46 (dd, J=4.83, 2.64Hz, 1H), 2.75 (dd, J=4.83, 3.96Hz, 1H), 2.83-2.96 (m, 1H), 3.49 (t, J=6.15Hz, 2H), 4.51 (s, 2H), 7.19-7.44 (m, 5H)

Reference Example 32: Synthesis of (2R)-2-[2-(benzyloxy)ethyl]oxirane

[0198] 

(1) (S)-Aspartic acid (25.04 g) and potassium bromide (102.98 g) were dissolved in 2.5 M sulfuric acid, and the solution was added dropwise with an aqueous solution (45 ml) of sodium nitrite (23.23 g) over 1 hour with maintaining the internal temperature to be in the range of -5 to 0°C on a sodium chloride-ice bath. After the addition, the reaction mixture was stirred for 2.5 hours with maintaining the internal temperature to be -5°C. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a bromo compound (33.18 g).

[0199] 

(2) The compound obtained in (1) mentioned above (12.92 g) was dissolved in tetrahydrofuran (100 ml), the solution was added with a solution of a boranetetrahydrofuran complex (1.01 M) in tetrahydrofuran (200 ml) on an ice bath, and the mixture was stirred at the same temperature for 3 hours. Then, the mixture was added with a mixed solvent of distilled water-tetrahydrofuran (1:1, 25 ml) on an ice bath. After the foaming ceased, the mixture was added with potassium carbonate (45.1 g), and the mixture was warmed to room temperature, and stirred for 1 hour. The reaction mixture was filtered, then the filtration residue was washed with diethyl ether, and the wash and the filtrate were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1 to 1:1) to obtain a diol compound (9.16 g).

[0200] 

(3) Sodium hydride (3.90 g) was added to tetrahydrofuran (108 ml), and then the mixture was slowly added dropwise with a solution of the compound obtained in (2) mentioned above (9.16 g) in tetrahydrofuran (20 ml) at an internal temperature in the range of -10 to -5°C on an ice-ethanol bath. The mixture was stirred for 30 minutes at the same temperature, and then added with benzyl bromide (7.1 ml) and tetra-n-butylammonium iodide (2.00 g), and the mixture was further stirred for 30 minutes at an internal temperature of -10°C. Then, the mixture was stirred at room temperature for 2 hours, and then added to saturated aqueous ammonium chloride, and the mixture was extracted with chloroform. The organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1 to 4:1) to obtain the title compound (5.22 g).
MS (ESI) m/z = 201.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.70-2.00 (m, 2H), 2.53 (dd, J=4.83, 2.64Hz, 1H), 2.79 (dd, J=5.05, 3.74Hz, 1H), 2.96-3.17 (m, 1H), 3.63 (t, J=6.59Hz, 2H), 4.54 (s, 2H), 7.29-7.39 (m, 5H)

Reference Example 33: Synthesis of 1-(oxiran-2-ylmethyl)piperidine

[0201] Piperidine (3 ml) was dissolved in t-butyl alcohol (1.2 ml), and the solution was added dropwise with (±)-epichlorohydrin (2.45 ml) on an ice bath. The mixture was slowly warmed to room temperature as it was, and stirred for 18 hours. Then, the mixture was added dropwise with a solution of potassium t-butoxide (3.39 g) in tetrahydrofuran (18 ml) under ice cooling so that the internal temperature should not exceed 15°C. After the addition, the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was added to distilled water, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 50:1) to obtain the title compound (1.55 g). MS (ESI) m/z = 142.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.36-1.52 (m, 2H), 1.53-1.70 (m, 4H), 2.29 (dd, J=13.19, 6.59Hz, 1H), 2.36-2.61 (m, 5H), 2.67 (m, 1H), 2.78 (dd, J=5.05, 4.18Hz, 1H), 3.05-3.16 (m, 1H)

Reference Example 34: Synthesis of benzyl 4-(oxiran-2-ylmethyl)piperazine-1-carboxylate

[0202] By using 1-benzyloxycarbonylpiperazine (6 ml) and (±)-epichlorohydrin (2.4 ml) as starting materials, the title compound (7.80 g)was obtained in the same manner as that of Reference Example 33.
MS (ESI) m/z = 299.2 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.27 (dd, J=13.40, 6.81Hz, 1H), 2.40-2.67 (m, 4H), 2.49 (dd, J=5.27, 2.64Hz, 1H), 2.72-2.86 (m, 2H), 3.04-3.17 (m, 1H), 3.56 (t, J=5.05Hz, 4H), 5.13 (s, 2H), 7.30-7.42 (m, 5H)

Reference Example 35: Synthesis of 1-(oxiran-2-ylmethyl)pyrrolidine

[0203] By using pyrrolidine (3 ml) and (±)-epichlorohydrin (2.9 ml) as starting materials, the title compound (2.10 g) was obtained in the same manner as that of Reference Example 33.
MS (ESI) m/z = 127.9 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.76-1.87 (m, 4H), 2.43 (dd, J=12.75, 6.59Hz, 1H), 2.49-2.56 (m, 1H), 2.55-2.69 (m, 4H), 2.73-2.86 (m, 2H), 3.06-3.19 (m, 1H)

Reference Example 36: Synthesis of (2R)-(4-azidobutyl)oxirane

[0204] 

(1) 6-Bromo-1-hexene (5.06 g) was dissolved in dimethyl sulfoxide (120 ml), the solution was added with sodium azide (2.42 g), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added to distilled water, the mixture was extracted with diethyl ether, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under ordinary pressure to obtain an azido compound (14.01 g).

[0205] 

(2) By using the compound obtained in (1) mentioned above (14.01 g) as a starting material, the title compound (6.26 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (TOF) = 142.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.43-1.79 (m, 6H), 2.48 (dd, J=4.83, 2.64Hz, 1H), 2.76 (dd, J=4.83, 3.96Hz, 1H), 2.85-2.99 (m, 1H), 3.30 (t, J=6.59Hz, 2H)

Reference Example 37: Synthesis of 3-nitrobenzyl [(2R)-oxiran-2-ylmethyl]carbamate

[0206] By using allyl isocyanate (0.7 g) and 3-nitrobenzyl alcohol (1.17 g) as starting materials, the title compound (1.7 g) was obtained in the same manners as those of Reference Example 29, (1) and Reference Example 26, (2).
MS (ESI) m/z = 275.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.62 (dd, J=4.61, 2.42Hz, 1H), 2.73-2.90 (m, 1H), 3.05-3.20 (m, 1H), 3.18-3.41 (m, 1H), 3.53-3.77 (m, 1H), 5.04 (s, 1H), 5.21 (s, 2H), 7.54 (t, J=7.69Hz, 1H), 7.63-7.74 (m, 1H), 8.12-8.28 (m, 2H)

Reference Example 38: 3-cyanobenzyl [(2R)-oxiran-2-ylmethyl]carbamate

[0207] By using allyl isocyanate (0.7 g) and 3-cyanobenzyl alcohol (1.02 g) as starting materials, the title compound (1.34 g) was obtained in the same manners as those of Reference Example 29, (1) and Reference Example 26, (2).
MS (ESI) m/z = 255.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.61 (dd, J=4.40, 2.64Hz, 1H), 2.76-2.85 (m, 1H), 3.06-3.18 (m, 1H), 3.19-3.35 (m, 1H), 3.55-3.76 (m, 1H), 4.91-5.08 (m, 1H), 5.14 (s, 2H), 7.39-7.71 (m, 4H)

Reference Example 39: Synthesis of oxiran-2-ylmethyl benzylcarbamate

[0208] 

(1) Benzylamine (5.0 g) was dissolved in chloroform (80 ml), the solution was added with saturated aqueous sodium hydrogencarbonate (80 ml) at room temperature, and then added with allyl chloroformate (6.75 g) under ice cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with chloroform, the layers were separated, and the organic layer was dried over
anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate:triethylamine = 10:10:0.2) to obtain a carbamate compound (8.86 g).

[0209] 

(2) By using the compound obtained in (1) mentioned above (8.86 g) as a starting material, the title compound (7.64 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 230.1 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 2.56-2.68 (m, 1H), 2.76-2.91 (m, 1H), 3.10-3.29 (m, 1H), 3.90 (dd, J=12.15, 6.19Hz, 1H), 4.36 (d, J=5.96Hz, 2H), 4.45 (dd, J=12.15, 2.98Hz, 1H), 5.08-5.22 (m, 1H), 7.15-7.42 (m, 5H)

Reference Example 40: Synthesis of pyridin-3-ylmethyl [(2R)-oxiran-2-ylmethyl]carbamate

[0210] 

(1) By using allyl isocyanate (1.0 g) and 3-pyridinemethanol (1.19 g) as starting materials, a carbamate compound (2.13 g) was obtained in the same manner as that of Reference Example 29, (1).

[0211] 

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (0.40 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 209.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 2.56-2.60 (m, 1H), 2.78 (t, J=4.36Hz, 1H), 3.10 (s, 1H), 3.22-3.29 (m, 1H), 3.59-3.66 (m, 1H), 5.00 (s, 1H), 5.12 (s, 2H), 7.29 (dd, J=7.79, 5.04Hz, 1H), 7.68 (d, J=7.79Hz, 1H), 8.55-8.58 (m, 1H), 8.61 (s, 1H)

Reference Example 41: Synthesis of 4-({3-[(2R)-oxiran-2-yl]propoxy}methyl)quinoline

[0212] 

(1) The compound obtained in Reference Example 21, (1) (1.5 g) was dissolved in tetrahydrofuran (50 ml), the solution was added with 4-(hydroxymethyl)quinoline (0.99 g) obtained by the method described in the literature (Synthesis, 1994, p.1278), potassium hydroxide (0.385 g) and 18-crown-6-ether (1.81 g), and the mixture was stirred at room temperature for 6 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 30:1) to obtain an ether compound (1.08 g).

[0213] 

(2) By using the compound obtained in (1) mentioned above (1.05 g) as a starting material, the title compound (0.46 g) was obtained in the same manners as those of Reference Example 7, (2) and Reference Example 1.
MS (ESI) m/z = 244.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.51-1.96 (m, 4H), 2.48 (dd, J=5.05, 2.86Hz, 1H), 2.72-2.80 (m, 1H), 2.90-3.02 (m, 1H), 3.63-3.73 (m, 2H), 4.98-5.01 (m, 2H), 7.49 (d, J=4.40Hz, 1H), 7.52-7.64 (m, 1H), 7.67-7.79 (m, 1H), 7.94-8.03 (m, 1H), 8.10-8.20 (m, 1H), 8.90 (d, J=4.40Hz, 1H)

Reference Example 42: Synthesis of 4-oxiran-2-ylbutanenitrile

[0214] By using 5-hexenenitrile (3.0 g) as a starting material, the title compound (5.03 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 134.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.45-1.69 (m, 1H), 1.74-1.97 (m, 3H), 2.33-2.56 (m, 3H), 2.74-2.82 (m, 1H), 2.87-3.02 (m, 1H)

Reference Example 43: Synthesis of methyl (oxiran-2-ylmethyl)carbamate

[0215] 

(1) Allylamine (4.5 ml) was dissolved in chloroform (50 ml), the solution was added dropwise with methyl chloroformate (2.32 ml) under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed successively with 2 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a carbamate compound (3.93 g).

[0216] 

(2) By using the compound obtained in (1) mentioned above (3.90 g) as a starting material, the title compound (3.32 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 154.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.61 (dd, J=4.83, 2.64Hz, 1H), 2.75-2.83 (m, 1H), 3.07-3.15 (m, 1H), 3.18-3.34 (m, 1H), 3.54-3.69 (m, 1H), 3.69 (s, 3H), 4.90 (br.s., 1H)

Reference Example 44: Synthesis of ethyl (oxiran-2-ylmethyl)carbamate

[0217] 

(1) By using allylamine (4.5 ml) and ethyl chloroformate (2.87 ml) as starting materials, a carbamate compound (5.84 g) was obtained in the same manner as that of Reference Example 43, (1).

(2) By using the compound obtained in (1) mentioned above (3.84 g) as a starting material, the title compound (2.43 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 168.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.25 (t, J=7.03Hz, 3H), 2.61 (dd, J=4.40, 2.64Hz, 1H), 2.73-2.86 (m, 1H), 3.06-3.15 (m, 1H), 3.18-3.34 (m, 1H), 3.52-3.68 (m, 1H), 4.13 (q, J=7.33Hz, 2H), 4.85 (br.s., 1H)

Reference Example 45: Synthesis of oxiran-2-ylmethyl methylcarbamate

[0218] By using 40% aqueous methylamine (7.3 ml) and allyl chloroformate (3 ml) as starting materials, the title compound (989 mg) was obtained in the same manners as those of Reference Example 43, (1) and Reference Example 26, (2).
MS (ESI) m/z = 154.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.61-2.67 (m, 1H), 2.78-2.87 (m, 1H), 2.81 (d, J=4.83Hz, 3H), 3.16-3.27 (m, 1H), 3.89 (dd, J=12.31, 6.59Hz, 1H), 4.44 (dd, J=12.31, 2.64Hz, 1H), 4.78 (br.s., 1H)

Reference Example 46: Synthesis of oxiran-2-ylmethyl dimethylcarbamate

[0219] By using 50% aqueous dimethylamine (9.03 ml) and allyl chloroformate (3 ml) as starting materials, the title compound (1.10 g) was obtained in the same manners as those of Reference Example 43, (1) and Reference Example 26, (2).
MS (ESI) m/z = 168.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.65 (dd, J=4.83, 2.64Hz, 1H), 2.84 (dd, J=4.83, 3.96Hz, 1H), 2.94 (s, 6H), 3.19-3.28 (m, 1H), 3.91 (dd, J=12.31, 6.15Hz, 1H), 4.44 (dd, J=12.31, 3.08Hz, 1H)

Reference Example 47: [3-(1,1-Dimethyl-3,5-dioxane-4-yl)phenyl]acetic acid

[0220] 

(1) (1,1-Dimethyl-3,5-dioxacyclohexan-4-yl)-3-bromomethylbenzene (0.90 g) obtained by the method described in the literature (Tetrahedron, 1997, vol. 53, p.6755) was dissolved in dimethyl sulfoxide (3 ml), the solution was added with sodium cyanide (0.17 g), and the mixture was stirred at 30°C for 2 hours. The mixture was further added with sodium cyanide (0.34 g), and the mixture was stirred at 30°C for 1 hour. The reaction mixture was added with 1 N aqueous sodium hydroxide and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a cyano compound (0.78 g).

[0221] 

(2) The compound obtained in (1) mentioned above (0.78 g) was dissolved in ethanol (10 ml), the solution was added with 5 N aqueous sodium hydroxide, and the mixture was stirred for 3 hours under reflux by heating. The reaction mixture was added with 3 N hydrochloric acid, thereby made acidic, and concentrated under reduced pressure, and the resulting residue was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (0.71 g).
MS (ESI) m/z = 273.0 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.80 (s, 3H), 1.29 (s, 3H), 3.60-3.69 (m, 4H), 3.73-3.81 (m, 2H), 5.39 (s, 1H), 7.29 (t, J=1.63Hz, 1H), 7.34 (t, J=7.77Hz, 1H), 7.39-7.46 (m, 2H)

Reference Example 48: Synthesis of 8-(2-aminoethoxy)-1-ethylquinolin-4(1H)-one hydrochloride

[0222] 

(1) 8-Benzyloxy-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (0.6 g) obtained by the method described in the patent document (WO04/101584) was dissolved in tetrahydrofuran (5 ml), the solution was added with 2 N aqueous sodium hydroxide (5 ml), and the mixture was stirred at 85°C for 2.5 hours. The reaction mixture was further added with ethanol (6 ml) and 2 N aqueous sodium hydroxide (6 ml), and the mixture was stirred at 85°C for 0.5 hour. The reaction mixture was concentrated under reduced pressure, and the concentrate was added with concentrated hydrochloric acid (2.5 ml). The deposited solid was separated by filtration, the resulting solid was washed with distilled water, and then dissolved in toluene, and the solution was filtered. The filtrate was concentrated under reduced pressure to obtain a carboxylic acid (0.5 g).

[0223] 

(2) The compound obtained in (1) mentioned above (0.5 g) was dissolved in dimethylformamide (10 ml), the solution was added with sodium cyanide (0.76 g), and the mixture was stirred at 120°C for 1 hour. The mixture was added with dimethyl sulfoxide (10 ml), the reaction mixture was stirred at 120°C for 8 hours, and then added with saturated aqueous ammonium chloride and diethyl ether, and the layers were separated. The organic layer was washed successively with 2 N aqueous sodium hydroxide and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 8-benzyloxy-1-ethyl-4-oxo-1,4-dihydroquinoline (20 mg). The aqueous layer was added with concentrated hydrochloric acid and thereby made acidic, and the deposited solid was separated by filtration. The resulting solid was dissolved in dimethyl sulfoxide (10 ml), the solution was added with sodium cyanide (0.5 g), and the mixture was stirred at 150°C for 12 hours and at 140°C for 11 hours. The reaction mixture was left to cool, and then added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to further obtain 8-benzyloxy-1-ethyl-4-oxo-1,4-dihydroquinoline (0.17 g).

[0224] 

(3) By using the compound obtained in (2) mentioned above (0.19 g) as a starting material, the title compound (0.1 g) was obtained according to the method described in the patent document (WO04/101584).
MS (ESI) m/z = 233.0 [M+H]^+
1H-NMR (200MHz, DMSO-d6) δ (ppm): 1.21-1.40 (m, 3H), 3.19-3.43 (m, 2H), 4.39 (t, J=5.27Hz, 2H), 4.52 (q, J=7.03Hz, 2H), 6.06 (d, J=7.47Hz, 1H), 7.22-7.45 (m, 2H), 7.77-8.01 (m, 2H)

Reference Example 49: Synthesis of 2-(1,2,3,4-tetrahydroquinolin-8-yloxy)ethanamine hydrochloride

[0225] 

(1) 8-Hydroxyquinoline (2 g) was dissolved in acetonitrile (50 ml), the solution was added with potassium carbonate (5.7 g) and N-(2-chloroethyl)dibenzylamine hydrochloride (4.1 g), and the mixture was stirred for 6 hours under reflux by heating. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was diluted with chloroform, washed successively with 2 N aqueous sodium hydroxide and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 3:1 to 0:1) to obtain a dibenzylamine compound (2.1 g).

[0226] 

(2) The compound obtained in (1) mentioned above (1 g) was dissolved in methanol (20 ml), the solution was added with 10% palladium-carbon (0.5 g) and concentrated hydrochloric acid (0.23 ml), and the mixture was stirred at room temperature for 12 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (20 ml), the solution was added with 10% palladium-carbon (0.5 g) and concentrated hydrochloric acid (0.23 ml), and the mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure to obtain the title compound (0.52 g).
MS (ESI) m/z = 193.0 [M+H]^+
1H-NMR (200MHz, CD₃ OD) δ (ppm): 1.94-2.16 (m, 2H), 2.86 (t, J=6.37Hz, 2H), 3.24-3.38 (m, 2H), 3.38-3.50 (m, 2H), 4.20-4.38 (m, 2H), 6.58-7.22 (m, 3H)

Reference Example 50: Synthesis of 2-phenoxyethylamine hydrochloride

[0227] By using phenol as a starting material, the title compound was obtained in the same manner as that of Reference Example 49.
MS (ESI) m/z = 137.9 [M+H]^+
1H-NMR (200MHz, DMSO-d6) δ (ppm): 3.19 (t, J=5.27Hz, 2H), 4.05-4.25 (m, 2H), 6.88-7.11 (m, 3H), 7.18-7.44 (m, 2H)

Reference Example 51: Synthesis of 8-(4-aminobutoxy)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

[0228] 

(1) 8-Hydroxy-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (300 mg) obtained by the method described in the patent document (WO04/101584) was dissolved in dimethylformamide (2 ml), the solution was added with 1,4-dibromobutane (737 mg) and potassium carbonate (159 mg), and the mixture was stirred at 100°C for 3 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was washed with distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in dimethylformamide (2 ml). The solution was added with dibenzylamine (343 mg) and potassium carbonate (238 mg), and the mixture was stirred at 100°C for 3 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was washed with distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a dibenzyl compound (343 mg).

[0229] 

(2) The compound obtained in (1) mentioned above (400 mg) was dissolved in tetrahydrofuran (4 ml), the solution was added with 2 N aqueous sodium hydroxide (2 ml), and the mixture was stirred at room temperature for 18 hours, and further stirred at 50°C for 2 hours. The reaction mixture was added with dry ice, and added with ethyl acetate. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in 4 N hydrochloric acid in dioxane (5 ml) and methanol (5 ml). The solution was added with 5% palladium-carbon (400 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol, the solution was added with a mixed solvent of hexane:ethyl acetate = 1:1 to deposit solid, and the solid was separated by filtration to obtain the title compound (71 mg).
¹H-NMR (300MHz, DMSO-d6) δ (ppm): 1.43 (t, J=6.92Hz, 3H), 1.70-2.01 (m, 2H), 3.27-3.52 (m, 2H), 4.24 (t, J=6.06Hz, 2H), 4.77-4.89 (m, 2H), 7.57-7.63 (m, 2H), 7.98-8.04 (m, 1H), 8.93 (s, 1H)

Reference Example 52: 2-(Quinolin-8-yloxy)ethanamine

[0230] 

(1) By using 8-quinolinol (1.0 g) and N-(2-bromoethyl)phthalimide (1.75 g) as starting materials, a phthalimide compound (230 mg) was obtained in the same manner as that of Reference Example 49 (1).

(2) The compound obtained in (1) mentioned above (220 mg) was dissolved in ethanol (3 ml), the solution was added with hydrazine monohydrate (50.4 µl), and the mixture was stirred for 4 hours under reflux by heating, and further stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with 1 N hydrochloric acid. The mixture was filtered, and then the filtrate was added with 5 N aqueous sodium hydroxide, and thereby made alkaline. The filtrate was added with chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (83 mg).
MS (ESI) m/z = 188.9 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 3.24-3.42 (m, 2H), 4.23-4.38 (m, 2H), 7.09 (dd, J=6.81, 1.98Hz, 1H), 7.33-7.54 (m, 3H), 8.05-8.24 (m, 1H), 8.96 (dd, J=4.18, 1.54Hz, 1H)

Reference Example 53: Synthesis of ethyl 1-ethyl-4-oxo-8-(3-oxopropoxy)-1,4-dihydroquinoline-3-carboxylate

[0231] 

(1) By using 8-hydroxy-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (0.2 g) obtained by the method described in the patent document (WO04/101584) and 3-bromo-1-propanol (0.13 g) as starting materials, an alcohol compound (223 mg) was obtained in the same manner as that of Reference Example 49, (1).

[0232] 

(2) The compound obtained in (1) mentioned above (46 mg) was dissolved in chloroform (3 ml), the solution was added with the Dess-Martin reagent (90 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (140 mg) in an unpurified state.

Reference Example 54: Synthesis of N-ethyl-N-[(1S)-1-(2-methoxyphenyl)ethyl]ethane-1,2-diamine

[0233] 

(1) (1S)-1-(2-Methoxyphenyl)ethanamine (8.86 g) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) was dissolved in chloroform (100 ml), the solution was added with acetic anhydride (12.0 g) and 4-dimethylaminopyridine (14.3 g), and the mixture was stirred at 70°C for 30 minutes. The reaction mixture was left to cool, then successively washed with 1 N hydrochloric acid and 10% aqueous sodium hydroxide, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an acetyl compound (11.23 g).

[0234] 

(2) Lithium aluminum hydride (3.3 g) was added to tetrahydrofuran (200 ml). The mixture was added with the compound obtained in (1) mentioned above (11.2 g) over 15 minutes under reflux by heating. The mixture was stirred for 3 hours under reflux by heating, then left to cool, and successively added with distilled water (3.3 ml), 15% aqueous sodium hydroxide (3.3 ml) and distilled water (3.3 ml), and the mixture was stirred for 2 hours. The reaction mixture was filtered, and the resulting filtrate was further washed with tetrahydrofuran. The filtrate and wash were concentrated under reduced pressure to obtain an N-ethyl compound (10.86 g).

[0235] 

(3) Phthalimide acetaldehyde (633 mg) obtained by the method described in the literature (Tetrahedron Letters, 2001, vol. 42, p.315) was dissolved in chloroform (20 ml), the solution was added with the compound obtained in (2) mentioned above (0.6 g) and sodium triacetoxyborohydride (1.06 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain a phthalimide compound (0.93 g).

[0236] 

(4) The compound obtained in (3) mentioned above (0.93 g) was dissolved in ethanol (20 ml), the solution was added with hydrazine monohydrate (0.38 ml), and the mixture was stirred for 3 hours under reflux by heating, and further stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with 1 N hydrochloric acid, and thereby made acidic, and the deposited solid was separated by filtration. The filtrate was neutralized with potassium carbonate, and then added with chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (484 mg).
MS (ESI) m/z = 223.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.98 (t, J=7.03Hz, 3H), 1.29 (d, J=7.03Hz, 3H), 2.38-2.72 (m, 6H), 3.82 (s, 3H), 4.37 (q, J=7.03Hz, 1H), 6.83-6.97 (m, 2H), 7.15-7.25 (m, 1H), 7.36 (dd, J=7.47, 1.76Hz, 1H)

Reference Example 55: Synthesis of 5-{ethyl[(1S)-1-(2-methoxyphenyl)ethyl]amino}pentanoic acid

[0237] 

(1) The compound obtained in Reference Example 54, (2) (1.0 g) was dissolved in dimethylformamide (5 ml), the solution was added with ethyl 5-bromopentanoate (1.21 g), and the mixture was stirred at 100°C for 2 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an ethyl ester (1.07 g).

[0238] 

(2) The compound obtained in (1) mentioned above (1.07 g) was dissolved in 3 N hydrochloric acid (15 ml), and the solution was stirred at 80°C for 5 hours. The reaction mixture was added with ethyl acetate, the layers were separated, and the organic layer was concentrated under reduced pressure. The resulting the residue was added with 10% aqueous sodium hydroxide, and the aqueous layer was extracted with ethyl acetate. The aqueous layer was neutralized with dry ice, the mixture was added with chloroform, and the layers were separated. The organic layer was concentrated under reduced pressure to obtain the title compound (201 mg).
MS (ESI) m/z = 280.1 [M+Na]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.15 (t, J=7.15Hz, 3H), 1.55 (d, J=6.68Hz, 3H), 1.53-1.80 (m, 4H), 2.08-2.31 (m, 2H), 2.68-2.86 (m, 3H), 2.91-3.04 (m, 1H), 3.83 (s, 3H), 4.65-4.79 (m, 1H), 6.88 (d, J=8.08Hz, 1H), 6.99 (t, J=7.54Hz, 1H), 7.28 (t, J=7.77Hz, 1H), 7.59 (d, J=7.31Hz, 1H)

Reference Example 56: Synthesis of 6-{ethyl[(1S)-1-(2-methoxyphenyl)ethyl]amino}hexanoic acid

[0239] By using the compound obtained in Reference Example 54, (2) (1.0 g) and ethyl 6-bromohexanoate (1.31 g) as starting materials, the title compound (400 mg) was obtained in the same manner as that of Reference Example 55.
MS(ESI) m/z= 294.1 [M+Na]^+
1H-NMR (300 MHz, CDCl₃) δ (ppm): 1.11 (t, J=7.15Hz, 3H), 1.21-1.35 (m, 2H), 1.49-1.68 (m, 4H), 1.52 (d, J=6.84Hz, 3H), 2.17-2.31 (m, 2H), 2.66-2.97 (m, 4H), 3.82 (s, 3H), 4.60 (q, J=6.42Hz, 1H), 6.87 (d, J=7.46Hz, 1H), 6.98 (t, J=7.31Hz, 1H), 7.22-7.29 (m, 1H), 7.61 (dd, J=7.69, 1.48Hz, 1H)

Reference Example 57: Synthesis of N-ethyl-N-[(1S)-1-(2-methoxyphenyl)ethyl]propane-1,3-diamine

[0240] 

(1) The compound obtained in Reference Example 54, (2) (1.0 g) was dissolved in dimethylformamide (10 ml), the solution was added with N-(3-bromopropyl)phthalimide (1.65 g) and potassium carbonate (0.85 g), and the mixture was stirred at 100°C for 2.5 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform alone to chloroform:methanol = 100:1 to 20:1) to obtain a phthalimide compound (1.58 g).

[0241] 

(2) By using the compound obtained in (1) mentioned above (1.73 g) as a starting material, the title compound (0.99 g) was obtained in the same manner as that of Reference Example 54, (4).
¹H-NMR (300MHz, CDCl₃) δ (ppm): 1.01 (t, J=7.07Hz, 3H), 1.28 (d, J=6.68Hz, 3H), 1.49-1.61 (m, 2H), 2.42-2.74 (m, 6H), 3.81 (s, 3H), 4.32 (q, J=6.84Hz, 1H), 6.86 (dd, J=8.24, 1.09Hz, 1H), 6.89-6.98 (m, 1H), 7.16-7.23 (m, 1H), 7.40 (dd, J=7.62, 1.71Hz, 1H)

Reference Example 58: Synthesis of N-ethyl-N-[(1S)-1-(2-methoxypheny)ethyl]butane-1,4-diamine

[0242] By using the compound obtained in Reference Example 54, (2) (1.0 g) and N-(4-bromobutyl)phthalimide (1.73 g) as starting materials, the title compound (0.98 g) was obtained in the same manners as those of Reference Example 57, (1) and Reference Example 54, (4).
¹H-NMR (300MHz, CDCl₃) δ (ppm): 0.99 (t, J=7.07Hz, 3H), 1.28 (d, J=6.68Hz, 3H), 1.30-1.58 (m, 4H), 2.35-2.72 (m, 6H), 3.81 (s, 3H), 4.30 (q, J=6.74Hz, 1H), 6.85 (dd, J=8.24,1.09Hz, 1H), 6.90-6.97 (m, 1H), 7.15-7.22 (m, 1H), 7.42 (dd, J=7.69, 1.79Hz, 1H)

Reference Example 59: Synthesis of 4-{ethyl[(1S)-1-(2-methoxyphenyl)ethyl]amino}butanoic acid

[0243] 

(1) Ethyl 4-bromobutanoate (5.0 g) was dissolved in toluene (100 ml), the solution was added with benzyl alcohol (51.3 ml) and concentrated hydrochloric acid (1 ml), and the mixture was heated with evaporating toluene. The reaction mixture was left to cool, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 10:1). The resulting compound was added with benzyl alcohol (250 ml) and p-toluenesulfonic acid monohydrate (100 mg), and the mixture was stirred at 100°C. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 10:1) to obtain benzyl 4-bromobutanoate (3.9 g).

[0244] 

(2) By using the compound obtained in (1) mentioned above (1.72 g) and the compound obtained in Reference Example 54, (2) (1.0 g) as starting materials, a benzyl ester compound (91 mg) was obtained in the same manner as that of Reference Example 55, (1).

[0245] 

(3) The compound obtained in (2) mentioned above (550 mg) was dissolved in tetrahydrofuran (10 ml), the solution was added with 5% palladium-carbon (200 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (560 mg).
MS (ESI) m/z = 266.1 [M+Na]^+
1H-NMR (300MHz, DMSO-d6) δ (ppm): 0.93 (t, J=6.99Hz, 3H), 1.22 (d, J=6.99Hz, 3H), 1.59 (t, 2H), 2.11 (t, J=7.23Hz, 2H), 2.31-2.64 (m, 4H), 3.76 (s, 3H), 4.28 (q, J=6.74Hz, 1H), 6.88-6.98 (m, 2H), 7.16-7.25 (m, 1H), 7.35 (dd, J=7.54, 1.63Hz, 1H)

Reference Example 60: Synthesis of N-(2-methoxyphenyl)propane-1,3-diamine

[0246] By using 3-bromopropylphthalimide (25.0 g) and o-anisidine (10 g) as starting materials, the title compound (4.9 g) was obtained in the same manners as those of Reference Example 57, (1) and Reference Example 54, (4).
MS (ESI) m/z = 180.9 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.74-1.95 (m, 2H), 2.87 (t, J=6.81Hz, 2H), 3.21 (t, J=6.81Hz, 2H), 3.84 (s, 3H), 6.56-6.92 (m, 4H)

Reference Example 61: Synthesis of N-benzyl-N-ethylethane-1,2-diamine

[0247] By using 2-bromoethylphthalimide and ethylbenzylamine as starting materials, the title compound (5.1 g) was obtained in the same manners as those of Reference Example 57, (1) and Reference Example 54, (4).
MS (ESI) m/z = 179.0 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.05 (t, J=7.15Hz, 3H), 2.46-2.59 (m, 4H), 2.73 (t, J=5.98Hz, 2H), 3.57 (s, 2H), 7.18-7.37 (m, 5H)

Reference Example 62: Synthesis ofN-[(1S)-1-(2-methoxyphenyl)ethyl]-N-methylethane-1,2-diamine

[0248] 

(1) (1S)-1-(2-Methoxyphenyl)ethanamine (100 mg) was dissolved in chloroform (10 ml), the solution was added with phthalimide acetaldehyde (125 mg) and sodium triacetoxyborohydride (210 mg), and the mixture was stirred at room temperature for 1 hour. The mixture was further added with 37% aqueous formaldehyde (340 ml) and sodium triacetoxyborohydride (210 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was
dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a phthalimide compound (244 mg).

[0249] 

(2) By using the compound obtained in (1) mentioned above as a starting material, the title compound (114 mg) was obtained in the same manner as that of Reference Example 54, (4).
¹H-NMR (600MHz, CDCl₃) δ (ppm): 1.29 (d, J=6.88Hz, 3H), 2.17 (s, 3H), 2.34-2.40 (m, 1H), 2.44-2.51 (m, 1H), 2.70-2.79 (m, 2H), 3.81 (s, 3H), 4.15 (q, J=6.88Hz, 1H), 6.86 (d, J=7.79Hz, 1H), 6.94 (m, 1H), 7.20 (m, 1H), 7.35 (dd, J=7.57, 1.60Hz, 1H)

Reference Example 63: Synthesis of N-ethyl-N-(1-pyrazin-2-ylethyl)ethane-1,2-diamine

[0250] 

(1) 1-(Pyrazin-2-yl)ethylamine (0.45 g) obtained by the method described in the patent document (WO0/100213) was dissolved in chloroform (20 ml), the solution was added with phthalimide acetaldehyde (0.76 g) and sodium triacetoxyborohydride (1.16 g), and the mixture was stirred at room temperature for 2 hours. The mixture was further added with acetaldehyde (0.342 ml) and sodium triacetoxyborohydride (1.16 g), and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an N-ethyl compound.

[0251] 

(2) By using the compound obtained in (1) mentioned above as a starting material, the title compound (0.66 g) was obtained in the same manner as that of Reference Example 54, (4).
MS (ESI) m/z = 195.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.04 (t, J=7.11Hz, 3H), 1.41 (d, J=6.88Hz, 3H), 2.45-2.52 (m, 2H), 2.55-2.64 (m, 2H), 2.65-2.74 (m, 2H), 4.09 (q, J=6.88Hz, 1H), 8.40 (d, J=2.29Hz, 1H), 8.47-8.50 (m, 1H), 8.72 (d, J=1.38Hz, 1H)

Reference Example 64: Synthesis of N-ethyl-N-[1-(2-methoxypyrazin-3-yl)ethyl]ethane-1,2-diamine

[0252] 

(1) 1-(2-Methoxy-3-pyrazinyl)-1-ethanone (0.5 g) obtained by the method described in the literature (Journal of Organic Chemistry, 1989, vol. 54, p.640) was dissolved in methanol, the solution was added with ammonium acetate (2.53 g) and sodium cyanoborohydride (0.145 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was added with 2 N hydrochloric acid, and the mixture was concentrated under reduced pressure, and then added with 5 N aqueous sodium hydroxide and thereby made alkaline. The mixture was added with chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain an amine compound (245 mg).

[0253] 

(2) By using the compound obtained in (1) mentioned above (245 mg) as a starting material, the title compound (53 mg) was obtained in the same manners as those of
Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 225.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.97 (t, J=7.25Hz, 3H), 1.35 (d, J=7.03Hz, 3H), 2.40-2.92 (m, 6H), 3.98 (s, 3H), 4.34-4.47 (m, 1H), 7.98 (d, J=2.64Hz, 1H), 8.07 (d, J=3.08Hz, 1H)

Reference Example 65: Synthesis of N-ethyl-N-(1-pyridin-3-ylethyl)ethane-1,2-diamine

[0254] By using 3-acetylpyridine (1.0 g) as a starting material, the title compound (146 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 194.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.33-1.42 (m, 3H), 2.35-2.60 (m, 4H), 2.63-2.73 (m, 2H), 3.93 (q, J=6.59Hz, 1H), 7.21-7.28 (m, 1H), 7.63-7.73 (m, 1H), 8.48 (dd, J=4.83, 1.76Hz, 1H), 8.60 (d, J=2.20Hz, 1H)

Reference Example 66: Synthesis of N-ethyl-N-[1-(4-methoxypyridin-3-yl)ethyl]ethane-1,2-diamine

[0255] By using 3-acetyl-4-methoxypyridine (500 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 10-287678) as a starting material, the title compound (97 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 224.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.98 (t, J=7.03Hz, 3H), 1.34 (d, J=7.03Hz, 3H), 2.39-2.74 (m, 6H), 3.87 (s, 3H), 4.32 (q, J=7.03Hz, 1H), 6.77 (d, J=5.71Hz, 1H), 8.39 (d, J=5.71Hz, 1H), 8.46 (s, 1H)

Reference Example 67: Synthesis of N,N-dimethyl-1,4-butanediamine

[0256] 

(1) N-Benzyloxycarbonyl-1,4-butanediamine (1.0 g) was dissolved in methanol (15 ml), and the solution was added with 37% aqueous formaldehyde (3.1 ml) and sodium triacetoxyborohydride (1.23 g). The mixture was stirred at room temperature for 2 hours, and then further added with sodium triacetoxyborohydride (820 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure to obtain a dimethylamino compound (950 mg).

(2) By using the compound obtained in (1) mentioned above (280 mg) as a starting material, the title compound (80 mg) was obtained in the same manner as that of Reference Example 4.
MS (GC) m/z = 293 [M-15]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 1.65 (quint, J=7.20Hz, 2H), 1.75 (quint, J=7.20Hz, 2H), 2.29 (s, 6H), 2.38 (t, J=7.20Hz, 2H), 2.87 (t, J=7.20Hz, 2H)

Reference Example 68: Synthesis of N-(2-aminomethyl)methanesulfonamide

[0257] 

(1) N-Benzyloxycarbonyl-1,2-diaminoethane hydrochloride (1.0 g) was suspended in dichloromethane (15 ml), the suspension was added with triethylamine (1.45 ml) and methanesulfonyl chloride (0.4 ml) under ice cooling, and the mixture was stirred for 20 minutes under ice cooling. The reaction mixture was added with distilled water, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain a methanesulfonyl compound (1.0 g).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (530 mg) was obtained in the same manner as that of Reference Example 4.
MS (GC) m/z = 139 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.91 (t, J=5.60Hz, 2H), 2.99 (s, 3H), 3.16 (t, J=5.60Hz, 2H)

Reference Example 69: Synthesis of N-(2-aminomethyl)acetamide

[0258] By using N-benzyloxycarbonyl-1,2-diaminoethane hydrochloride (1.0 g) and acetyl chloride (370 µl) as starting materials, the title compound (440 mg) was obtained in the same manners as those of Reference Example 68, (1) and Reference Example 4.
MS (GC) m/z = 103 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.01 (s, 3H), 2.84 (t, J=6.00Hz, 2H), 3.16 (q, J=5.6Hz, 2H), 6.01 (brs, 1H)

Reference Example 70: Synthesis of 1-[1-(2-methoxyphenyl)ethyl]pyrrolidin-3-amine

[0259] 3-t-Butoxycarbonylaminopyrrolidine (560 mg) was dissolved in methanol (5 ml), the solution was added with acetic acid (170 µl), 2-methoxyacetophenone (140 µl) and sodium cyanoborohydride (45 mg), and the mixture was stirred at 50°C for 20 hours. The reaction mixture was added with 5 N hydrochloric acid (10 ml), the mixture was stirred at room temperature for 2 hours, and then made basic with potassium carbonate, and methanol was evaporated under reduced pressure. The reaction mixture was added with chloroform, the layers were separated, the organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain the title compound (83 mg).
MS (ESI) m/z = 221 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 1.30-1.33 (m, 3H), 1.38-1.52 (m, 1H), 2.12-2.21 (m, 1H), 2.26-2.35 (m, 1H), 2.37-2.56 (m, 1H), 2.60-2.81 (m, 2H), 3.44-3.50 (m, 1H), 3.78-3.84 (m, 4H), 6.86 (d, J=8.28Hz, 1H), 6.94-6.99 (m, 1H), 7.17-7.21 (m, 1H), 7.49-7.52 (m, 1H)

Reference Example 71: Synthesis of 1-[1-(2-methoxyphenyl)ethyl]piperazine

[0260] By using N-t-butoxycarbonylpiperazine (560 mg) as a starting material, the title compound (149 mg) was obtained in the same manner as that of Reference Example 70.
MS (ESI) m/z = 221 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 1.30 (d, J=6.80Hz, 3H), 2.32-2.56 (m, 4H), 2.86 (t, J=4.80Hz, 4H), 3.81 (s, 3H), 3.93 (q, J=6.80Hz, 1H), 6.84-6.89 (m, 1H), 6.92-6.98 (m, 1H), 7.17-7.22 (m, 1H), 7.40-7.45 (m, 1H)

Reference Example 72: Synthesis of N-ethyl-N-[(1S)-1-(3-methoxyphenyl)ethyl]ethane-1,2-diamine

[0261] By using (S)-1-(3-methoxyphenyl)ethylamine (200 mg) as a starting material, the title compound (135 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 223.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.25Hz, 3H), 1.33 (d, J=6.59Hz, 3H), 2.35-2.76 (m, 6H), 3.77-3.92 (m, 1H), 3.81 (s, 3H), 6.72-6.82 (m, 1H), 6.89-7.01 (m, 2H), 7.16-7.28 (m, 1H)

Reference Example 73: Synthesis of N-ethyl-N-[(1S)-1-(4-methoxyphenyl)ethyl]ethane-1,2-diamine

[0262] By using (S)-1-(4-methoxyphenyl)ethylamine (200 mg) as a starting material, the title compound (167 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 223.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.25Hz, 3H), 1.32 (d, J=6.59Hz, 3H), 2.31-2.77 (m, 6H), 3.75-3.94 (m, 1H), 3.80 (s, 3H), 6.85 (d, J=8.79Hz, 2H), 7.27 (d, J=8.79Hz, 2H)

Reference Example 74: Synthesis of N-ethyl-N-[(1S)-1-(4-fluorophenyl)ethyl]ethane-1,2-diamine

[0263] By using (S)-1-(4-fluorophenyl)ethylamine (200 mg) as a starting material, the title compound (186 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 211.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.03Hz, 3H), 1.32 (d, J=6.59Hz, 3H), 2.33-2.73 (m, 6H), 3.80-3.93 (m, 1H), 6.99 (t, J=8.79Hz, 2H), 7.27-7.36 (m, 2H)

Reference Example 75: Synthesis of N-[(1S)-1-(4-chlorophenyl)ethyl]-N-ethylethane-1,2-diamine

[0264] By using (S)-4-chloro-α-methylbenzylamine (200 mg) as a starting material, the title compound (179 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 227.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.01 (t, J=7.25Hz, 3H), 1.32 (d, J=7.03Hz, 3H), 2.33-2.74 (m, 6H), 3.85 (q, J=6.59Hz, 1H), 7.24-7.34 (m, 4H)

Reference Example 76: Synthesis of N-ethyl-N-[(1S)-1-(4-methylphenyl)ethyl]ethane-1,2-diamine

[0265] By using (S)-1-(p-tolyl)-ethylamine (200 mg) as a starting material, the title compound (219 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 207.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.03Hz, 3H), 1.33 (d, J=7.03Hz, 3H), 2.33 (s, 3H), 2.34-2.72 (m, 6H), 3.77-3.93 (m, 1H), 7.06-7.26 (m, 4H)

Reference Example 77: Synthesis of N-ethyl-N-[(1S)-1-(2-fluorophenyl)ethyl]ethane-1,2-diamine

[0266] By using (S)-1-(2-fluorophenyl)ethylamine (200 mg) as a starting material, the title compound (236 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 211.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.99 (t, J=7.11Hz, 3H), 1.34 (d, J=6.88Hz, 3H), 2.38-2.69 (m, 6H), 4.26 (q, J=6.88Hz, 1H), 6.96-7.02 (m, 1H), 7.05-7.12 (m, 1H), 7.15-7.21 (m, 1H), 7.32-7.39 (m, 1H)

Reference Example 78: Synthesis of N-[1-[4-(benzyloxy)phenyl]ethyl]-N-ethylethane-1,2-diamine

[0267] 

(1) 4'-hydroxyacetophenone (3.0 g) was dissolved in acetone (50 ml), the solution was added with benzyl bromide (2.88 ml) and potassium carbonate (4.57 g), and the mixture was stirred for 4 hours under reflux by heating. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a benzyl ether compound (5.0 g).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (161 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 298.9 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.25Hz, 3H), 1.33 (d, J=7.03Hz, 3H), 2.31-2.73 (m, 6H), 3.85 (q, J=6.74Hz, 1H), 5.05 (s, 2H), 6.93 (d, J=8.79Hz, 2H), 7.19-7.50 (m,7H)

Reference Example 79: Synthesis of N-ethyl-N-[1-(3-fluorophenyl)ethyl]ethane-1,2-diamine

[0268] 

(1) By using 3'-fluoroacetophenone (5.0 g) as a starting material, an amine compound (2.77 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (525 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 211.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.03Hz, 3H), 1.33 (d, J=7.03Hz, 3H), 2.32-2.78 (m, 6H), 3.87 (q, J=6.89Hz, 1H), 6.82-7.00 (m, 1H), 7.02-7.17 (m, 2H), 7.19-7.33 (m, 1H)

Reference Example 80: Synthesis of N-[1-(3-chlorophenyl)ethyl]-N-ethylethane-1,2-diamine

[0269] 

(1) By using 3'-chloroacetophenone (5.0 g) as a starting material, an amine compound (2.62 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (474 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 227.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.03Hz, 3H), 1.33 (d, J=7.03Hz, 3H), 2.36-2.73 (m, 6H), 3.85 (q, J=6.74Hz, 1H), 7.14-7.40 (m, 4H)

Reference Example 81: Synthesis of N-[1-(4-ethoxyphenyl)ethyl]-N-ethylethane-1,2-diamine

[0270] 

(1) By using 4'-ethoxyacetophenone (5.0 g) as a starting material, an amine compound (3.58 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (532 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 237.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.03Hz, 3H), 1.32 (d, J=7.03Hz, 3H), 1.41 (t, J=7.03Hz, 3H), 2.32-2.71 (m, 6H), 3.84 (q, J=6.59Hz, 1H), 4.02 (q, J=7.03Hz, 2H), 6.84 (d, J=8.79Hz, 2H), 7.25 (d, J=8.35Hz, 2H)

Reference Example 82: Synthesis of N-[1-(1-methyl-1H-pyrrol-3-yl)ethyl]ethane-1,2-diamine

[0271] 3-Acetyl-1-methylpyrrole (1.0 g) and ethylenediamine (1.46 g) were dissolved in toluene (10 ml), the solution was added with p-toluenesulfonic acid monohydrate (154 mg), and the mixture was refluxed for 2 hours by heating. The reaction mixture was added to a suspension of sodium borohydride (307 mg) in tetrahydrofuran, then the mixture was added with methanol, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was made acidic with 1 N hydrochloric acid, and then the solvent was evaporated under reduced pressure. The mixture was added with distilled water and potassium carbonate, and thereby neutralized, and then the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (1.14 g).
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.37 (d, J=6.59Hz, 3H), 2.35-2.67 (m, 2H), 2.72-2.83 (m, 2H), 3.06 (s, 3H), 3.87 (q, J=6.59Hz, 1H), 7.55 (d, J=8.35Hz, 2H), 7.89 (d, J=8.79Hz, 2H)

Reference Example 83: Synthesis of N-ethyl-N-[1-(2-methylphenyl)ethyl]ethane-1,2-diamine

[0272] 

(1) By using 2'-methylacetophenone (5.0 g) as a starting material, an amine compound (2.05 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (514 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 207.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.25Hz, 3H), 1.30 (d, J=7.03Hz, 3H), 2.27-2.74 (m, 6H), 2.41 (s, 3H), 4.08 (q, J=6.59Hz, 1H), 7.07-7.23 (m, 3H), 7.32-7.43 (m, 1H)

Reference Example 84: Synthesis of N-ethyl-N-[1-(3-methylphenyl)ethyl]ethane-1,2-diamine

[0273] 

(1) By using 3'-methylacetophenone (5.0 g) as a starting material, an amine compound (3.06 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (550 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 207.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.34 (d, J=7.03Hz, 3H), 2.35 (s, 3H), 2.37-2.73 (m, 6H), 3.84 (q, J=6.74Hz, 1H), 6.99-7.25 (m, 4H)

Reference Example 85: Synthesis of N-ethyl-N-[1-(4-ethylphenyl)ethyl]ethane-1,2-diamine

[0274] 

(1) By using 4'-ethylacetophenone (5.0 g) as a starting material, an amine compound (3.10 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (675 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).

MS (ESI) m/z = 221.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.24 (t, J=7.69Hz, 3H), 1.34 (d, J=6.59Hz, 3H), 2.33-2.71 (m, 8H), 3.80-3.92 (m, 1H), 7.10-7.18 (m, 2H), 7.21-7.30 (m, 2H)

Reference Example 86: Synthesis of N-[1-[3-(dimethylamino)phenyl]ethyl]-N-ethylethane-1,2-diamine

[0275] 

(1) By using 3'-dimethylaminoacetophenone (5.0 g) as a starting material, an amine compound (2.46 g) was obtained in the same manner as that of Reference Example 64, (1).

(2) By using the compound obtained in (1) mentioned above (1.0 g) as a starting material, the title compound (396 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 236.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.35 (d, J=6.59Hz, 3H), 2.37-2.74 (m, 6H), 2.94 (s, 6H), 3.81 (q, J=6.89Hz, 1H), 6.56-6.81 (m, 3H), 7.18 (t, J=7.91Hz, 1H)

Reference Example 87: Synthesis of N-ethyl-N-[1-(3-nitrophenyl)ethyl]ethane-1,2-diamine

[0276] By using 3'-nitroacetophenone (500 mg) as a starting material, the title compound (71 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 238.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.11Hz, 3H), 1.38 (d, J=6.42Hz, 3H), 2.42-2.62 (m, 4H), 2.66-2.75 (m, 2H), 3.97 (q, J=6.57Hz, 1H), 7.47 (t, J=8.02Hz, 1H), 7.72 (d, J=7.34Hz, 1H), 8.06-8.11 (m, 1H), 8.21-8.25 (m, 1H)

Reference Example 88: Synthesis of N-ethyl-N-[(1S)-1-[2-(trifluoromethyl)phenyl]ethyl]ethane-1,2-diamine

[0277] By using (S)-1-[2-(trifluoromethyl)phenyl]ethylamine (200 mg) as a starting material, the title compound (115 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 261.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.97 (t, J=7.03Hz, 3H), 1.31 (d, J=6.59Hz, 3H), 2.28-2.51 (m, 1H), 2.52-2.86 (m, 5H), 4.01-4.23 (m, 1H), 7.23-7.36 (m, 1H), 7.44-7.65 (m, 2H), 7.85 (d, J=7.91Hz, 1H)

Reference Example 89: Synthesis of N-ethyl-N-[(1S)-1-[3-(trifluoromethyl)phenyl]ethyl]ethane-1,2-diamine

[0278] By using (S)-1-[3-(trifluoromethyl)phenyl]ethylamine (200 mg) as a starting material, the title compound (98 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 261.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.36 (d, J=6.59Hz, 3H), 2.32-2.78 (m, 6H), 3.86-3.99 (m, 1H), 7.33-7.67 (m, 4H)

Reference Example 90: Synthesis of N-ethyl-N-[(1S)-1-[4-(trifluoromethyl)phenyl]ethyl]ethane-1,2-diamine

[0279] By using (S)-1-[4-(trifluoromethyl)phenyl]ethylamine (200 mg) as a starting material, the title compound (108 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 261.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.36 (d, J=7.03Hz, 3H), 2.32-2.77 (m, 6H), 3.92 (q, J=6.74Hz, 1H), 7.42-7.61 (m, 4H)

Reference Example 91: Synthesis of N-[(1S)-1-(4-bromophenyl)ethyl]-N-ethylethane-1,2-diamine

[0280] By using (S)-1-(4-bromophenyl)ethylamine (200 mg) as a starting material, the title compound (61 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 271.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.01 (t, J=7.25Hz, 3H), 1.31 (d, J=7.03Hz, 3H), 2.32-2.76 (m, 6H), 3.83 (q, J=6.74Hz, 1H), 7.18-7.29 (m, 2H), 7.37-7.48 (m, 2H)

[0281] Reference Example 92: Synthesis of N-ethyl-N-[(1S)-1-phenylethyl]ethane-1,2-diamine

(1) By using (S)-(-)-1-phenylethylamine (210 mg) as a starting material, the title compound (230 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 193.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.96 (t, J=7.11Hz, 3H), 1.28 (d, J=6.88Hz, 3H), 1.50 (brs, 2H), 2.33-2.63 (m, 6H), 3.81 (q, J=6.72Hz, 1H), 7.13-7.18 (m, 1H), 7.22-7.26 (m, 2H), 7.27-7.30 (m, 2H)

Reference Example 93: Synthesis of N-ethyl-N-[(1S)-1-(1-naphthyl)ethyl]ethane-1,2-diamine

[0282] 

(1) By using (S)-(-)-1-(1-naphthyl)ethylamine (240 mg) as a starting material, the title compound (220 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 243.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.06 (t, J=7.11Hz, 3H), 1.25 (brs, 2H), 1.44 (d, J=6.42Hz, 3H), 2.36-2.56 (m, 4H), 2.69 (q, J=7.18Hz, 2H), 4.65 (q, J=6.57Hz, 1H), 7.33-7.55 (m, 4H), 7.71 (d, J=8.25Hz, 1H), 7.80 (d, J=7.79Hz, 1H), 8.42 (d, J=8.25Hz, 1H)

Reference Example 94: Synthesis of N-ethyl-N-[(1S)-1-(2-naphthyl)ethyl]ethane-1,2-diamine

[0283] 

(1) By using (S)-(-)-1-(2-naphthyl)ethylamine (240 mg) as a starting material, the title compound (160 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 243.1 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 1.04 (t, J=7.11Hz, 3H), 1.43 (brs, 2H), 1.39-1.46 (d, J=6.88Hz, 3H), 2.43-2.72 (m, 6H), 4.02 (q, J=6.72Hz, 1H), 7.41-7.49 (m, 2H), 7.54-7.60 (m, 2H), 7.70 (s, 1H), 7.75-7.83 (m, 2H)

Reference Example 95: Synthesis of N-[1-(1-methyl-1H-pyrrol-2-yl)ethyl]ethane-1,2-diamine

[0284] By using 2-acetyl-1-methylpyrrole (1.0 g) as a starting material, the title compound (424 mg) was obtained in the same manner as that of Reference Example 82.
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.43 (d, J=6.59Hz, 3H), 2.51-2.80 (m, 4H), 3.66 (s, 3H), 3.87 (q, J=6.59Hz, 1H), 5.99-6.08 (m, 2H), 6.52-6.56 (m, 1H)

Reference Example 96: Synthesis of N-[1-[4-(methylsulfonyl)phenyl]ethyl]ethane-1,2-diamine

[0285] 4'-(Methylsulfonyl)acetophenone (1.0 g) and ethylenediamine (908 mg) were dissolved in methanol (10 ml), and the solution was heated at 50°C for 3 hours. The reaction mixture was added with a suspension of sodium borohydride (286 mg) in tetrahydrofuran (50 ml), and then added with methanol (6 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was made acidic with 1 N hydrochloric acid, and then the solvent was evaporated under reduced pressure. The mixture was added with distilled water and potassium carbonate and thereby neutralized, then the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (553 mg).
MS (ESI) m/z = 243.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.37 (d, J=6.59Hz, 3H), 2.35-2.67 (m, 2H), 2.72-2.83 (m, 2H), 3.06 (s, 3H), 3.87 (q, J=6.59Hz, 1H), 7.55 (d, J=8.35Hz, 2H), 7.89 (d, J=8.79Hz, 2H)

Reference Example 97: Synthesis of N-[1-(1-ethyl-1H-pyrazol-5-yl)ethyl]ethane-1,2-diamine

[0286] By using 1-(2-ethyl-2H-pyrazol-3-yl)-ethanone (250 mg) as a starting material, the title compound (72 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 183.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.40-1.49 (m, 6H), 2.47-2.82 (m, 4H), 3.95 (q, J=6.59Hz, 1H), 4.21 (q, J=7.03Hz, 2H), 6.12 (d, J=1.76Hz, 1H), 7.43 (d, J=1.76Hz, 1H)

Reference Example 98: Synthesis of 3-[1-[(2-aminoethyl)amino]ethyl]-N-methylthiophene-2-sulfonamide

[0287] By using 3-acetyl-2-(methylaminosulfonyl)thiophene (1.0 g) as a starting material, the title compound (762 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 264.1 [M+H]⁺

Reference Example 99: Synthesis of N-[1-(1-methyl-1H-pyrazol-5-yl)ethyl]ethane-1,2-diamine

[0288] By using 1-(2-methyl-2H-pyrazol-3-yl)-ethanone (250 mg) as a starting material, the title compound (34 mg) was obtained in the same manner as that of Reference Example 82.
¹H-NMR, (200MHz, CDCl₃) δ (ppm): 1.42 (d, J=6.59Hz, 3H), 2.50-2.88 (m, 4H), 3.90-4.02 (m, 1H), 4.14 (s, 3H), 6.45-6.52 (m, 1H), 7.37-7.45 (m, 1H)

Reference Example 100: Synthesis of N-[1-(1,3-dimethyl-1H-pyrazol-5-yl)ethyl]ethane-1,2-diamine

[0289] By using 1-(2,5-dimethyl-2H-pyrazol-3-yl)-ethanone (250 mg) as a starting material, the title compound (57 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 183.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.39 (d, J=6.59Hz, 3H), 2.23 (s, 3H), 2.49-2.68 (m, 2H), 2.73-2.83 (m, 2H), 3.81 (s, 3H), 3.88 (q, J=6.59Hz, 1H), 5.91 (s, 1H)

Reference Example 101: Synthesis of N-(1-[3-[(diethylamino)methyl]-4-methoxyphenyl]ethyl)ethane-1,2-diamine

[0290] By using 1-(3-[(diethylamino)methyl]-4-methoxyphenyl)ethanone (250 mg) as a starting material, the title compound (130 mg) was obtained in the same manner as that of Reference Example 82.
¹H-NMR (200MHz, CDCl₃) δ (ppm): 0.97-1.15 (m, 6H), 1.31-1.38 (m, 3H), 2.43-2.80 (m, 8H), 3.53-3.62 (m, 2H), 3.64-3.78 (m, 1H), 3.78-3.84 (m, 3H), 6.75-6.86 (m, 1H), 7.09-7.19 (m, 1H), 7.27-7.37 (m, 1H)

Reference Example 102: Synthesis of N-[1-[4-methoxy-3-(pyrrolidin-1-ylmethyl)phenyl]ethyl]ethane-1,2-diamine

[0291] By using 1-[4-methoxy-3-(pyrrolidin-1-ylmethyl)phenyl]ethanone (250 mg) as a starting material, the title compound (70 mg) was obtained in the same manner as that of Reference Example 82.
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.34 (d, J=6.59Hz, 3H), 1.73-1.86 (m, 4H), 2.40-2.79 (m, 8H), 3.63-3.78 (m, 3H), 3.81 (s, 3H), 6.77-6.87 (m, 1H), 7.11-7.30 (m, 2H)

Reference Example 103: Synthesis of 2-[1-[(2-aminoethyl)amino]ethyl]phenol

[0292] By using 2'-hydroxyacetophenone (1.0 g) as a starting material, the title compound (303 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 181.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.47 (d, J=6.59Hz, 3H), 2.61-2.71 (m, 2H), 2.74-3.03 (m, 2H), 3.92 (q, J=6.74Hz, 1H), 6.71-6.84 (m, 2H), 6.91-7.00 (m, 1H), 7.08-7.19 (m, 1H)

Reference Example 104: Synthesis of N-[1-(2-nitrophenyl)ethyl]ethane-1,2-diamine

[0293] By using 2'-nitroacetophenone (1.0 g) as a starting material, the title compound (110 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 210.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.44 (d, J=6.59Hz, 3H), 2.30-2.47 (m, 1H), 2.50-2.65 (m, 1H), 2.69-2.81 (m, 2H), 4.28 (q, J=6.59Hz, 1H), 7.29-7.42 (m, 1H), 7.52-7.65 (m, 1H), 7.70-7.84 (m, 2H)

Reference Example 105: Synthesis of N-[1-(2-chlorophenyl)ethyl]ethane-1,2-diamine

[0294] By using 2'-chloroacetophenone (1.0 g) as a starting material, the title compound (529 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 199.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.41-2.66 (m, 2H), 2.73-2.83 (m, 2H), 4.29 (q, J=6.59Hz, 1H), 7.09-7.37 (m, 3H), 7.47-7.54 (m, 1H)

Reference Example 106: Synthesis of 3-[1-[(2-aminoethyl)amino]ethyl]phenol

[0295] 3'-Hydroxyacetophenone (1.0 g) and ethylenediamine (1.47 ml) were dissolved in methanol (10 ml), and the solution was stirred at room temperature for 16 hours. The mixture was added with sodium borohydride (277.9 mg), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with 1 N hydrochloric acid, and then the solvent was evaporated. The residue was added with potassium carbonate and distilled water, thereby made alkaline, and then extracted with a mixed solvent of chloroform-ethanol (10:1), and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1 to 5:1:0.1) to obtain the title compound (59.1 mg).
MS (ESI) m/z = 181.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.36 (d, J=6.59Hz, 3H), 2.44-2.85 (m, 4H), 3.72 (q, J=6.45Hz, 1H), 6.63-6.91 (m, 3H), 7.09-7.21 (m, 1H)

Reference Example 107: Synthesis of N-[1-(2-ethoxyphenyl)ethyl]ethane-1,2-diamine

[0296] By using 2'-ethoxyacetophenone (1.0 g) as a starting material, the title compound (882 mg) was obtained in the same manner as that of Reference Example 106.
MS (ESI) m/z = 209.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.33-1.48 (m, 6H), 2.46-2.59 (m, 2H), 2.70-2.84 (m, 2H), 3.97-4.20 (m, 3H), 6.80-6.98 (m, 2H), 7.11-7.34 (m, 2H)

Reference Example 108: Synthesis of N-[1-(4-nitrophenyl)ethyl]ethane-1,2-diamine

[0297] By using 4'-nitroacetophenone (1.0 g) as a starting material, the title compound (639 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 210.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.37 (d, J=6.59Hz, 3H), 2.35-2.49 (m, 1H), 2.52-2.67 (m, 1H), 2.73-2.82 (m, 2H), 3.89 (q, J=6.59Hz, 1H), 7.51 (d, J=8.79Hz, 2H), 8.19 (d, J=8.79Hz, 2H)

Reference Example 109: Synthesis of N-[1-(3-methoxyphenyl)ethyl]ethane-1,2-diamine

[0298] By using 3'-methoxyacetophenone (1.0 g) as a starting material, the title compound (1.16 g) was obtained in the same manner as that of Reference Example 106.
MS (ESI) m/z = 195.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.36 (d, J=6.59Hz, 3H), 2.41-2.65 (m, 2H), 2.72-2.81 (m, 2H), 3.74 (q, J=6.30Hz, 1H), 3.81 (s, 3H), 6.73-6.82 (m, 1H), 6.86-6.95 (m, 2H), 7.17-7.31 (m, 1H)

Reference Example 110: Synthesis of 4-[1-[(2-aminoethyl)amino]ethyl]phenol

[0299] By using 4'-hydroxyacetophenone (1.0 g) as a starting material, the title compound (59.1 mg) was obtained in the same manner as that of Reference Example 106.
MS (ESI) m/z = 181.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.42-2.86 (m, 4H), 3.62-3.79 (m, 1H), 6.65 (d, J=8.79Hz, 2H), 7.11 (d, J=8.35Hz, 2H)

Reference Example 111: Synthesis of N-[1-[4-(dimethylamino)phenyl]ethyl]ethane-1,2-diamine

[0300] By using 4'-dimethylaminoacetophenone (1.0 g) as a starting material, the title compound (370 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 208.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.41-2.65 (m, 2H), 2.70-2.81 (m, 2H), 2.93 (s, 6H), 3.62-3.76 (m, 1H), 6.72 (d, J=8.79Hz, 2H), 7.18 (d, J=8.79Hz, 2H)

Reference Example 112: Synthesis of N-[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-N-ethylethane-1,2-diamine

[0301] By using (S)-1-[3,5-bis(trifluoromethyl)phenyl]ethylamine (210 mg) as a starting material, the title compound (210 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 329.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.04 (t, J=7.03Hz, 3H), 1.39 (d, J=6.59Hz, 3H), 1.51 (br.s., 2H), 2.38-2.78 (m, 6H), 3.98 (q,1H), 7.75 (s, 1H), 7.85 (s, 2H)

Reference Example 113: Synthesis of N-ethyl-N-[(1R)-1-(3-methoxyphenyl)ethyl]ethane-1,2-diamine

[0302] By using (R)-1-(3-methoxyphenyl)ethylamine (500 mg) as a starting material, the title compound (390 mg) was obtained in the same manners as those of Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 223.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.03Hz, 3H), 1.34 (d, J=7.03Hz, 3H), 2.36-2.75 (m, 6H), 3.78-3.91 (m, 1H), 3.81 (s, 3H), 6.72-6.82 (m, 1H), 6.84-6.99 (m, 2H), 7.16-7.28 (m, 1H)

Reference Example 114: Synthesis of 4-[1-[(2-aminoethyl)amino]ethyl]-2-[(diethylamino)methyl]phenol

[0303] By using 1-(3-[(diethylamino)methyl]-4-hydroxyphenyl)ethanone (250 mg) as a starting material, the title compound (89 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 266.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.10 (t, J=7.03Hz, 6H), 1.33 (d, J=6.59Hz, 3H), 2.41-2.79 (m, 8H), 3.66 (q, J=6.59Hz, 1H), 3.75 (s, 2H), 6.74 (d, J=7.91Hz, 1H), 6.89-6.94 (m, 1H), 7.03-7.11 (m, 1H)

Reference Example 115: Synthesis of 4-[1-[(2-aminoethyl)amino]ethyl]-2-(piperidin-1-ylmethyl)phenol

[0304] By using 1-(4-hydroxy-3-piperidin-1-ylmethyl-phenyl)-ethanone (250 mg) as a starting material, the title compound (137 mg) was obtained in the same manner as that of Reference Example 82.
MS (ESI) m/z = 300.2 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.42-1.70 (m, 6H), 2.37-2.82 (m, 8H), 3.59-3.73 (m, 3H), 6.75 (d, J=8.35Hz, 1H), 6.87-6.95 (m, 3H), 7.03-7.11 (m, 3H)

Reference Example 116: Synthesis of N-[1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethyl]ethane-1,2-diamine

[0305] By using 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone (250 mg) as a starting material, the title compound (69 mg) was obtained in the same manner as that of Reference Example 96.
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 1.39-1.67 (m, 6H), 2.39-2.79 (m, 8H), 3.54 (s, 2H), 3.72 (q, J=6.59Hz, 1H), 3.80 (s, 3H), 6.82 (d, J=8.35Hz, 1H), 7.12-7.20 (m, 1H), 7.24-7.32 (m, 1H)

Reference Example 117: Synthesis of N-[1-[4-methoxy-3-(morpholin-4-ylmethyl)phenyl]ethyl]ethane-1,2-diamine

[0306] By using 1-[4-methoxy-3-(morpholin-4-ylmethyl)phenyl]ethanone (250 mg) as a starting material, the title compound (181 mg) was obtained in the same manner as that of Reference Example 96.
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.41-2.80 (m, 8H), 3.56 (s, 2H), 3.66-3.76 (m, 5H), 3.81 (s, 3H), 6.83 (d, J=8.35Hz, 1H), 7.13-7.30 (m, 2H)

Reference Example 118: Synthesis of 2-(4-[1-[(2-aminoethyl)amino]ethyl]phenoxy)-N,N-dimethylacetamide

[0307] By using 2-(4-acetylphenoxy)-N,N-dimethylacetamide (250 mg) as a starting material, the title compound (162 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 266.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.33 (d, J=6.59Hz, 3H), 2.36-2.65 (m, 2H), 2.69-2.82 (m, 2H), 2.99 (s, 3H), 3.10 (s, 3H), 3.72 (q, J=6.59Hz, 1H), 4.67 (s, 2H), 6.86-6.94 (m, 2H), 7.18-7.29 (m, 2H)

Reference Example 119: Synthesis of N-[1-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]ethyl]ethane-1,2-diamine

[0308] By using 1-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]ethanone (250 mg) as a starting material, the title compound (168 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 308.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.34 (d, J=6.59Hz, 3H), 2.39-2.82 (m, 4H), 3.56-3.78 (m, 9H), 4.68 (s, 2H), 6.90 (d, J=8.79Hz, 2H), 7.17-7.30 (m, 2H)

Reference Example 120: Synthesis of N-[1-[4-(4-methylpiperazin-1-yl)phenyl]ethyl]ethane-1,2-diamine

[0309] By using 1-[4-(4-methylpiperazino)phenyl]-1-ethanone (250 mg) as a starting material, the title compound (62 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 263.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.34 (d, J=6.59Hz, 3H), 2.35 (s, 3H), 2.41-2.80 (m, 8H), 3.15-3.24 (m, 4H), 3.70 (q, J=6.59Hz, 1H), 6.89 (d, J=8.79Hz, 2H), 7.20 (d, J=8.35Hz, 2H)

Reference Example 121: Synthesis of N-(3-[1-[(2-aminoethyl)amino]ethyl]phenyl)methanesulfonamide

[0310] By using N-(3-acetylphenyl)methanesulfonamide (250 mg) as a starting material, the title compound (189 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 258.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.37-2.87 (m, 4H), 3.02 (s, 3H), 3.70-3.85 (m, 1H), 7.05-7.39 (m, 4H)

Reference Example 122: Synthesis of 1-(4-[1-[(2-aminoethyl)amino]ethyl]phenyl)pyridin-4(1H)-one

[0311] By using 1-(4-acetylphenyl)pyridin-4(1H)-one (250 mg) as a starting material, the title compound (287 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 258.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.38 (d, J=6.59Hz, 3H), 2.36-2.71 (m, 2H), 2.72-2.87 (m, 2H), 3.85 (q, J=6.74Hz, 1H), 6.50 (d, J=7.47Hz, 2H), 7.21-7.35 (m, 2H), 7.40-7.65 (m, 4H)

Reference Example 123: Synthesis of 1-[4-[1-[(2-aminoethyl)amino]ethyl]phenyl]piperidin-4-ol

[0312] By using 1-[4-(4-hydroxypiperidin-1-yl)phenyl]ethanone (250 mg) as a starting material, the title compound (146 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 264.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.36 (d, J=6.59Hz, 3H), 1.57-1.82 (m, 2H), 1.92-2.11 (m, 2H), 2.39-2.66 (m, 2H), 2.69-3.03 (m, 4H), 3.42-3.95 (m, 4H), 6.90 (d, J=8.35Hz, 2H), 7.19 (d, J=8.35Hz, 2H)

Reference Example 124: Synthesis of N'-[3-[1-[(2-aminoethyl)amino]ethyl]phenyl]-N,N-dimethylsulfamide

[0313] By using N'-(3-acetylphenyl)-N,N-dimethylsulfamide (250 mg) as a starting material, the title compound (299 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 287.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.33-2.82 (m, 4H), 2.85 (s, 6H), 3.69-3.83 (m, 1H), 7.00-7.33 (m, 4H)

Reference Example 125: Synthesis of N-[1-[4-(2-pyridin-4-ylaziridin-1-yl)phenyl]ethyl]ethane-1,2-diamine

[0314] By using 1-[4-(2-pyridin-4-ylaziridin-1-yl)phenyl]ethanone (250 mg) as a starting material, the title compound (272 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 283.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.35 (d, J=6.59Hz, 3H), 2.32-2.66 (m, 4H), 2.69-2.83 (m, 2H), 3.05 (dd, J=6.37, 3.30Hz, 1H), 3.73 (q, J=6.30Hz, 1H), 6.98 (d, J=8.35Hz, 2H), 7.22 (d, J=8.35Hz, 2H), 7.30 (d, J=6.15Hz, 2H), 8.57 (d, J=6.15Hz, 2H)

Reference Example 126: Synthesis of N-[1-(1-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

[0315] 1-(1-Methyl-1H-pyrazol-4-yl)-ethanone (250 mg) and ethylenediamine (362 mg) were dissolved in methanol (10 ml), the solution was added with acetic acid (1.21 g) and sodium cyanoborohydride (189 mg), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and tetrahydrofuran, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (163 mg).
MS (ESI) m/z = 169.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.26 (d, J=6.59Hz, 3H), 2.53-2.80 (m, 4H), 3.69 (q, J=6.59Hz, 1H), 3.77 (s, 3H), 7.34 (s, 1H), 7.53 (s, 1H)

Reference Example 127: Synthesis of 4-[1-[(2-aminoethyl)amino]ethyl]benzenesulfonamide

[0316] By using 4-acetyl-benzenesulfonamide (250 mg) as a starting material, the title compound (49 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 244.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.22 (d, J=6.15Hz, 3H), 2.36-2.68 (m, 4H), 3.64-3.83 (m, 1H), 7.45-7.56 (m, 2H), 7.70-7.82 (m, 2H)

Reference Example 128: Synthesis of N-[(1S)-1-(2-methoxyphenyl)ethyl]ethane-1,2-diamine

[0317] By using (1S)-1-(2-methoxyphenyl)ethylamine (70 mg) as a starting material, the title compound (71 mg) was obtained in the same manners as those of Reference Example 54, (3) and (4).
MS (ESI) m/z = 195.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.36 (d, J=6.59Hz, 3H), 2.47-2.58 (m, 2H), 2.71-2.82 (m, 2H), 3.83 (s, 3H), 4.12 (q, J=6.59Hz, 1H), 6.82-7.01 (m, 2H), 7.13-7.36 (m, 2H)

Reference Example 129: Synthesis of N-[1-(3-ethylphenyl)ethyl]ethane-1,2-diamine

[0318] By using 3'-ethylacetophenone (500 mg) as a starting material, the title compound (571 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 193.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.24 (t, J=7.47Hz, 3H), 1.37 (d, J=6.59Hz, 3H), 2.38-2.85 (m, 6H), 3.74 (q, J=6.89Hz, 1H), 7.02-7.31 (m, 4H)

Reference Example 130: Synthesis of N-[1-[4-(4,5-bis[[(triethylsilyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]ethyl]ethane-1,2-diamine

[0319] 

(1) 1-[4-(4,5-Bis[[(triethylsilyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)phenyl]ethanone (100 mg) was dissolved in dimethylformamide (2 ml), the solution was added with t-butyldimethylchlorosilane (134.1 mg) and imidazole (165.2 mg), and the mixture was stirred at room temperature for 16 hours and at 50°C for 6 hours. The mixture was further added with t-butyldimethylchlorosilane (134.1 mg) and imidazole (165.2 mg), and the mixture was stirred at room temperature for 16 hours. The mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform) to obtain a protected compound (199 mg).

(2) By using the compound obtained in (1) mentioned above (195 mg) as a starting material, the title compound (138 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 520.4 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.00 (s, 6H), 0.13 (s, 6H), 0.82 (s, 9H), 0.92 (s, 9H), 1.39 (d, J=6.59Hz, 3H), 2.42-2.69 (m, 2H), 2.73-2.85 (m, 2H), 3.78-3.95 (m, 1H), 4.77 (s, 2H), 4.92 (s, 2H), 7.41-7.66 (m, 4H)

Reference Example 131: Synthesis of 3-[(1S)-1-[(2-aminoethyl)amino]ethyl]phenol

[0320] By using (S)-1-(3-hydroxyphenyl)ethylamine (400 mg) obtained by the method described in the literature (Journal Medicinal Chemistry, 2004, vol. 47, p.2887) as a starting material, the title compound (71 mg) was obtained in the same manners as those of Reference Example 54, (3) and (4).
¹H-NMR (600MHz, CDCl₃) δ (ppm): 1.34 (d, J=6.42Hz, 3H), 2.49-2.55 (m, 1H), 2.59-2.64 (m, 1H), 2.72-2.80 (m, 2H), 3.70 (q, J=6.57Hz, 1H), 6.68 (dd, J=8.02, 2.52Hz, 1H), 6.80 (d, J=7.34Hz, 1H), 6.82-6.85 (m, 1H), 7.15 (t, J=7.79Hz, 1H)

Reference Example 132: Synthesis of N-[1-[4-[[t-butyl(dimethyl)silyl]oxy]-3,5-dimethoxyphenyl]ethyl]ethane-1,2-diamine

[0321] 3',5'-Dimethoxy-4'-hydroxyacetophenone (1.00 g) was dissolved in dimethylformamide (4 ml), the solution was added with imidazole (1.04 g) and t-butyldimethylchlorosilane (769 mg), and the mixture was stirred at room temperature for 10 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was successively washed 3 times with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. This product was dissolved in methanol (20 ml), the solution was added with ethylenediamine (289 mg), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added with a suspension of sodium borohydride (289 mg) in tetrahydrofuran (30 ml), and then added with methanol (6 ml), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (417 mg).
MS (ESI) m/z = 355.3 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.12 (s, 6H), 1.01 (s, 9H), 1.34 (d, J=6.59Hz, 3H), 2.40-2.66 (m, 2H), 2.71-2.81 (m, 2H), 3.60-3.73 (m, 1H), 3.79 (s, 6H), 6.50 (s, 2H)

Reference Example 133: Synthesis of 2-amino-3-(dimethylamino)propan-1-ol

[0322] Lithium aluminum hydride (555 mg) was suspended in tetrahydrofuran (30 ml), the suspension was added with 4-aza-DL-leucine dihydrochloride (2.0 g) under reflux by heating, and the mixture was stirred for 3 hours. The reaction mixture was added successively with distilled water, 15% aqueous sodium hydroxide and distilled water, and the mixture was stirred for 12 hours. The reaction mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain the title compound (140 mg).
MS (ESI) m/z = 119.0 [M+H]^+
1H-NMR (600MHz, DMSO-d6) δ (ppm): 2.08-2.16 (m, 1H), 2.11 (s, 6H), 3.20-3.39 (m, 4H)

Reference Example 134: Synthesis of 1-methylpyrrolidin-3-amine

[0323] By using 3-amino-1-N-t-butoxycarbonyl-pyrrolidine (2.0 g) as a starting material, the title compound (240 mg) was obtained in the same manner as that of Reference Example 133.
MS (ESI) m/z = 101.0 [M+H]⁺

Reference Example 135: Synthesis of 2-(4-methylpiperazin-1-yl)ethanamine

[0324] 

(1) 1-Methylpiperazine (873 µl) was dissolved in dimethylformamide (20 ml), the solution was added with N-(2-bromoethyl)phthalimide (1.0 g), and the mixture was stirred at room temperature for 52 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was successively washed twice with distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 100:10:0.2) to obtain a phthalimide compound (580 mg).

(2) The compound obtained in (1) mentioned above (580 mg) was dissolved in ethanol (20 ml), the solution was added with hydrazine monohydrate (515 µl), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (90 mg).
MS (ESI) m/z = 144.0 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 2.27 (s, 3H), 2.36-2.61 (m, 10H), 2.78 (t, J=6.19Hz, 2H)

Reference Example 136: Synthesis of benzyl 4-(2-aminoethyl)piperazine-1-carboxylate

[0325] N-(2-Aminoethyl)piperazine (4.93 g) was dissolved in tetrahydrofuran (40 ml), and the solution was added with triethylamine (10.6 ml). The mixture was added with a solution of benzyl chloroformate (4.9 ml) in tetrahydrofuran (40 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (400 mg).
MS (ESI) m/z = 264.0 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 2.37-2.45 (m, 6H), 2.79 (t, J=6.19Hz, 2H), 3.49-3.53 (m, 4H), 5.12 (s, 2H), 7.28-7.37 (m, 5H)

Reference Example 137: Synthesis of (1R,2R)-2-[(5-aminopentyl)amino]-1-(4-nitrophenyl)propane-1,3-diol

[0326] 

(1) (1S,2S)-(+)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (5.0 g) was dissolved in dimethylformamide (50 ml), the solution was added with N-(5-bromopentyl)phthalimide (7.8 g), and the mixture was stirred at 70°C for 6 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and then the organic layer was washed twice with distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 40:1:0.1) to obtain a phthalimide compound (3.0 g).

(2) The compound obtained in (1) mentioned above (1.0 g) was dissolved in ethanol (10 ml), the solution was added with hydrazine monohydrate (340 µl), and the mixture was heated for 4 hours with stirring. The reaction mixture was concentrated under reduced pressure, and then added with 1 N hydrochloric acid, and the mixture was stirred and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form, chloroform:methanol = 9:1) to obtain the title compound (130 mg).
MS (ESI) m/z = 298.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.20-1.56 (m, 4H), 2.32-2.77 (m,7H), 3.35 (dd, J=11.21, 3.74Hz, 1H), 3.60-3.75 (m, 1H), 4.69 (d, J=7.03Hz, 1H), 7.59 (d, J=8.79Hz, 2H), 8.19 (d, J=8.79Hz, 2H)

Reference Example 138: Synthesis of (1R,2R)-2-[(6-aminohexyl)amino]-1-(4-nitrophenyl)propane-1,3-diol

[0327] 

(1) By using (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol (5.0 g) and N-(6-bromohexyl)phthalimide (8.16 g) as starting materials, a phthalimide compound (6.1 g) was obtained in the same manner as that of Reference Example 137, (1).

(2) By using the compound obtained in (1) mentioned above (3.0 g) as a starting material, the title compound (1.05 g) was obtained in the same manner as that of Reference Example 137, (2).
MS (ESI) m/z = 312.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.19-1.55 (m, 6H), 2.25-2.73 (m,7H), 3.37 (dd, J=11.21, 3.74Hz, 1H), 3.70 (dd, J=11.21, 3.74Hz, 1H), 4.69 (d, J=6.59Hz, 1H), 7.59 (d, J=8.35Hz, 2H), 8.20 (d, J=8.79Hz, 2H)

Reference Example 139: Synthesis of (1R,2R)-2-[(2-aminoethyl)amino]-1-(4-nitrophenyl)propane-1,3-diol

[0328] 

(1) (1S,2S)-(+)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (3.0 g) was dissolved in dimethylformamide (30 ml), the solution was added with N-(2-bromoethyl)phthalimide (4.30 g) and triethylamine (2.85 g), and the mixture was stirred at 70°C for 10 hours. The reaction mixture was added with ethyl acetate and distilled water, and the layers were separated, and then the organic layer was washed twice with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 40:1:0.1) to obtain a phthalimide compound (1.94 g).

(2) The compound obtained in (1) mentioned above (1.94 g) was dissolved in ethanol (100 ml), the solution was added with hydrazine monohydrate (755 mg), and the mixture was refluxed by heating for 10 hours. The reaction mixture was concentrated under reduced pressure, and then added with 1 N hydrochloric acid, and the mixture was stirred, and then filtered. The filtrate was made basic with 10% aqueous sodium hydroxide, and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (1.35 g).
MS (ESI) m/z = 256.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.64-2.92 (m, 5H), 3.33-3.47 (m, 1H), 3.67 (dd, J=11.65, 3.74Hz, 1H), 4.63 (d, J=7.03Hz, 1H), 7.58 (d, J=8.35Hz, 2H), 8.21 (d, J=9.23Hz, 2H)

Reference Example 140: Synthesis of (1R,2R)-2-[(3-aminopropyl)amino]-1-(4-nitrophenyl)propane-1,3-diol

[0329] By using (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol (3.0 g) and N-(3-bromopropyl)phthalimide (4.53 g) as starting materials, the title compound (2.54 g) was obtained in the same manner as that of Reference Example 139.
MS (ESI) m/z = 270.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.55-1.74 (m, 2H), 2.48-2.90 (m, 5H), 3.39 (dd, J=11.43, 3.96Hz, 1H), 3.61-3.83 (m, 1H), 4.69 (d, J=7.03Hz, 1H), 7.59 (d, J=8.35Hz, 2H), 8.20 (d, J=8.79Hz, 2H)

Reference Example 141: Synthesis of (1R,2R)-2-[(4-aminobutyl)amino]-1-(4-nitrophenyl)propane-1,3-diol

[0330] By using (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol (3.0 g) and N-(4-bromobutyl)phthalimide (4.77 g) as starting materials, the title compound (2.76 g) was obtained in the same manner as that of Reference Example 139.
MS (ESI) m/z = 284.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.41-1.56 (m, 4H), 2.33-2.76 (m, 5H), 3.37 (dd, J=11.43, 3.96Hz, 1H), 3.63-3.76 (m, 1H), 4.69 (d, J=7.03Hz, 1H), 7.59 (d, J=8.35Hz, 2H), 8.20 (d, J=8.79Hz, 2H)

Reference Example 142: Synthesis of N-(2-[[t-butyl(dimethyl)silyl]oxy]ethyl)-N-ethylethane-1,2-diamine

[0331] 

(1) 2-Ethylaminoethanol (5.0 g) was dissolved in dimethylformamide (100 ml), the solution was added with imidazole (22.9 g) and t-butyldimethylchlorosilane (16.9 g), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a protected compound (786 mg).

(2) The compound obtained in (1) mentioned above (410 mg) and phthalimide acetaldehyde (419 mg) were dissolved in chloroform (5 ml), the solution was added with sodium triacetoxyborohydride (642 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 5:1) to obtain a phthalimide compound. This phthalimide compound was dissolved in ethanol, the solution was added with hydrazine monohydrate (0.29 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the deposited solid was separated by filtration and washed with ethanol. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (294 mg).
MS (ESI) m/z = 247.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.06 (s, 6H), 0.90 (s, 9H), 0.94-1.10 (m, 3H), 2.47-2.77 (m, 8H), 3.66 (t, J=6.59Hz, 2H)

Reference Example 143: Synthesis of 2-amino-1-(4-nitrophenyl)ethanol

[0332] 

(1) 4-Nitrostyrene (2.0 g) was dissolved in a mixed solvent of acetonitrile-distilled water (3:2, 50 ml), the solution was added with N-bromosuccinimide (2.63 g), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and then extracted with diethyl ether, and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in methanol (130 ml). The solution was added with potassium carbonate (1.5 g), and the mixture was stirred at room temperature for 4 hours. The mixture was added with distilled water, the mixture was concentrated under reduced pressure, and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an epoxy compound (2.67 g).

(2) The compound obtained in (1) mentioned above (500 mg) was added with a 8 N solution of ammonia in methanol (5 ml), and the mixture was stirred at room temperature for 1 day. The reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the title compound (221 mg).
MS (ESI) m/z = 183.0 [M+H]^+
1H-NMR (200MHz, DMSO-d6) δ (ppm): 2.52-2.80 (m, 2H), 4.51-4.68 (m, 1H), 5.46-5.68 (m, 1H), 7.60 (d, J=8.35Hz, 2H), 8.19 (d, J=8.79Hz, 2H)

Reference Example 144: Synthesis of 2-amino-3-(4-nitrophenyl)propan-1-ol

[0333] Lithium aluminum hydride (271 mg) was suspended in tetrahydrofuran, the suspension was added with 4-nitro-DL-phenylalanine (1.0 g) under ice cooling, and the mixture was stirred for 1 hour. The reaction mixture was added successively with distilled water, 15% aqueous sodium hydroxide and distilled water, and the mixture was stirred for 12 hours. The reaction mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain the title compound (516 mg).
MS (ESI) m/z = 197.0 [M+H]^+
1H-NMR (600MHz, DMSO-d6) δ (ppm): 2.50-2.54 (m, 1H), 2.79-2.89 (m, 2H), 3.16-3.27 (m, 2H), 4.64-4.69 (m, 1H), 7.47 (d, J=8.71Hz, 2H), 8.12 (d, J=8.71Hz, 2H)

Reference Example 145: Synthesis of N-(2-[[t-butyl(dimethyl)silyl]oxy]ethyl)-N-[(1S)-1-(2-methoxyphenyl)ethyl]ethane-1,2-diamine

[0334] 

(1) (R)-1-(2-Methoxyphenyl)ethylamine (250 mg) and (2-bromoethoxy)-t-butyldimethylsilane (396 mg) were dissolved in dimethylformamide (5 ml), and the solution was stirred at 100°C for 4 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 60:1:0.1) to obtain an adduct compound (407 mg).

(2) By using the compound obtained in (1) mentioned above (400 mg) as a starting material, the title compound (268 mg) was obtained in the same manners as those of Reference Example 54, (3) and (4).
¹H-NMR (200MHz, CDCl₃) δ (ppm): 0.00 (s, 6H), 0.86 (s, 9H), 1.31 (d, J=7.03Hz, 3H), 2.38-2.86 (m, 6H), 3.40-3.69 (m, 2H), 3.81 (s, 3H), 4.38 (q, J=6.89Hz, 1H), 6.80-6.99 (m, 2H), 7.11-7.39 (m, 2H)

Reference Example 146: Synthesis of 4-[[2-[[t-butyl(dimethyl)silyl]oxy]ethyl](ethyl)amino]butan-1-ol

[0335] The compound obtained in Reference Example 142, (1) (1.0 g) was dissolved in dimethylformamide (50 ml), the solution was added with potassium carbonate (3.3 g) and 4-bromo-1-butanol (1.13 g), and the mixture was stirred at 100°C for 2 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and then the organic layer was washed twice with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain the title compound (77 mg).
MS (ESI) m/z = 276.3 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 0.06 (s, 6H), 0.89 (s, 9H), 1.01 (t, J=7.03Hz, 3H), 1.44-1.72 (m, 4H), 2.41-2.64 (m, 6H), 3.40-3.49 (m, 2H), 3.59-3.72 (m, 2H)

[0336] Reference Example 147: Synthesis of 1-amino-3-[(2-methoxyphenyl)amino]propan-2-ol

(1) N-(2,3-Epoxypropyl)phthalimide (800 mg) and o-anisidine (485 mg) were dissolved in ethanol (10 ml), and the solution was stirred for 6 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:1 to 1:3) to obtain an adduct compound (831 mg).

(2) By using the compound obtained in (1) mentioned above (816 mg) as a starting material, the title compound (170 mg) was obtained in the same manner as that of Reference Example 54, (4).
MS (ESI) m/z = 197.1 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.96-3.44 (m, 4H), 3.84 (s, 3H), 4.11-4.30 (m, 1H), 4.36-4.56 (m, 1H), 6.56-6.95 (m, 4H)

Reference Example 148: Synthesis of 1-amino-3-[ethyl[(1S)-1-(2-methoxyphenyl)ethyl]amino]propan-2-ol

[0337] 

(1) By using N-(2,3-epoxypropyl)phthalimide (470 mg) and (1S)-1-(2-methoxyphenyl)ethanamine (350 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) as starting materials, an adduct compound (495 mg) was obtained in the same manner as that of Reference Example 147, (1).

(2) By using the compound obtained in (1) mentioned above (485 mg) and acetaldehyde (334 mg) as starting materials, an N-ethyl compound (452 mg) was obtained in the same manner as that of Reference Example 54, (3).

(3) By using the compound obtained in (2) mentioned above (441 mg) as a starting material, the title compound (296 mg) was obtained in the same manner as that of Reference Example 54, (4).
MS (ESI) m/z = 253.2 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (pom): 0.86-1.07 (m, 3H), 1.23-1.38 (m, 3H), 2.33-2.80 (m, 6H), 3.45-3.72 (m, 1H), 3.79-3.90 (m, 3H), 4.33-4.50 (m, 1H), 6.82-7.39 (m, 4H)

Reference Example 149: Synthesis of N-(5-aminopentyl)-2,2-dichloroacetamide

[0338] 

(1) 5-Amino-1-pentanol (1.0 g) was dissolved in tetrahydrofuran (10 ml), the solution was added with a solution of dichloroacetyl chloride (1.0 ml) in tetrahydrofuran (10 ml) under ice cooling, and the mixture was stirred at room temperature for 1 hour.
The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 40:1:0.1) to obtain a dichloroacetyl compound (446 mg).

(2) The compound obtained in (1) mentioned above (445 mg) was dissolved in chloroform (10 ml), the solution was added with pyridine (10 ml) and a solution of p-toluenesulfonyl chloride (5.94 g) in chloroform (20 ml) under ice cooling, and the mixture was stirred at room temperature for 12 hours. The mixture was added with saturated brine and chloroform, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 6:1) to obtain a p-toluenesulfonyl compound (204 mg).

(3) The compound obtained in (2) mentioned above (204 mg) was dissolved in dimethylformamide (2 ml), the solution was added with potassium phthalimide (154 mg), and the mixture was stirred at 70°C for 2 hours and at 100°C for 2 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1) to obtain a phthalimide compound (160 mg).

(4) The compound obtained in (3) mentioned above (160 mg) was dissolved in ethanol (3 ml), the solution was added with hydrazine monohydrate (67.8 µl), and the mixture was stirred at 80°C for 4 hours. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (47 mg).
MS (ESI) m/z = 213.0 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.29-1.87 (m, 6H), 2.71 (t, J=6.59Hz, 2H), 3.25-3.42 (m, 2H), 5.95 (s, 1H), 6.85-7.10 (m, 1H)

Reference Example 150: Synthesis of N-(3-[[t-butyl(dimethyl)silyl]oxy]propyl)-N-ethylethane-1,2-diamine

[0339] 

(1) N-(2-Bromoethyl)phthalimide (9 g) was dissolved in dimethylformamide (25 ml), the solution was added with ethylbenzylamine (5.27 g) and potassium carbonate (5.39 g), and the mixture was stirred at 100°C for 6 hours. The reaction mixture was added with 2 N hydrochloric acid and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was added with a mixed solvent of ethyl acetate-hexane(1:1), and the deposited crystals were dried under reduced pressure to obtain a phthalimide compound (8.43 g).

(2) By using the compound obtained in (1) mentioned above (485 mg) as a starting material, a debenzylated compound (1.50 g) was obtained in the same manner as that of Reference Example 7, (3).

(3) The compound obtained in (2) mentioned above (500 mg) was dissolved in dimethylformamide (10 ml), the solution was added with (3-bromopropoxy)-t-butyldimethylsilane (796 µl) and potassium carbonate (475 mg), and the mixture was stirred at 100°C for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 10:1) to obtain an adduct compound (387 mg).

(4) By using the compound obtained in (3) mentioned above (387 mg) as a starting material, the title compound (191 mg) was obtained in the same manner as that of Reference Example 54, (4).
MS (ESI) m/z = 261.3 [M+H]+
¹H-NMR (200MHz, CDCl₃) δ (ppm): 0.01-0.10 (m, 6H), 0.89 (s, 9H), 0.95-1.11 (m, 3H), 1.52-1.75 (m, 3H), 2.40-2.65 (m, 5H), 2.66-2.77 (m, 2H), 3.54-3.73 (m, 2H)

Reference Example 151: Synthesis of 6-(dimethylamino)hexanal

[0340] By using 6-dimethylamino-1-hexanol (100 mg) as a starting material, the title compound (37.8 mg) was obtained in the same manner as that of Reference Example 53, (2).
¹H-NMR (200MHz, CDCl₃) δ (ppm): 1.28-1.79 (m, 6H), 2.25-2.61 (m, 4H), 2.36 (s, 6H), 9.72-9.80 (m, 1H)

Reference Example 152: Synthesis of t-butyl(dimethyl)[[(1R)-1-methyl-3-oxiran-2-ylpropyl]oxy]silane

[0341] 

(1) (R)-(-)-5-Hexen-2-ol (1 g) was dissolved in dimethylformamide (10 ml), the solution was added with imidazole (2.04 g) and t-butyldimethylchlorosilane (2.26 g) under ice cooling, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 40:1) to obtain a protected compound (1.7 g).

(2) By using the compound obtained in (1) mentioned above (1.7 g) as a starting material, the title compound (1.58 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 253.1 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.02-0.05 (m, 6H), 0.85-0.88 (m, 9H), 1.10-1.15 (m, 3H), 1.44-1.68 (m, 4H), 2.44-2.47 (m, 1H), 2.72-2.75 (m, 1H), 2.88-2.93 (m, 1H), 3.75-3.87 (m, 1H)

Reference Example 153: Synthesis of t-butyl(dimethyl)[[(1S)-1-methyl-3-oxiran-2-ylpropyl]oxy] silane

[0342] By using (S)-(+)-5-hexen-2-ol (1 g) as a starting material, the title compound (1.48 g) was obtained in the same manners as those of Reference Example 152, (1) and Reference Example 26, (2).
MS (ESI) m/z = 253.1 [M+Na]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.01-0.05 (m, 6H), 0.85-0.89 (m, 9H), 1.10-1.14 (m, 3H), 1.44-1.68 (m, 4H), 2.43-2.47 (m, 1H), 2.72-2.75 (m, 1H), 2.88-2.93 (m, 1H), 3.77-3.87 (m, 1H)

Reference Example 154: Synthesis of 3-(oxiran-2-ylmethyl)-1,3-oxazolidin-2-one

[0343] 

(1) 2-Oxazolidinone (3 g) was dissolved in acetone (130 ml), the solution was added with allyl bromide (5.8 ml) and cesium carbonate (33.7 g), and the mixture was stirred at 60°C for 24 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain an adduct compound (4.18 g).

(2) By using the compound obtained in (1) mentioned above (4.10 g) as a starting material, the title compound (511 mg) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 143.8 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 2.54-2.65 (m, 1H), 2.79-2.86 (m, 1H), 2.97-3.19 (m, 2H), 3.55-3.93 (m, 3H), 4.29-4.44 (m, 2H)

Reference Example 155: Synthesis of 3-(2-oxiran-2-ylethyl)-1,3-oxazolidin-2-one

[0344] By using 2-oxazolidinone (2.20 g) and 4-bromo-1-butene (4.42 g) as starting materials, the title compound (389 mg) was obtained in the same manners as those of Reference Example 154, (1) and Reference Example 26, (2).
MS (ESI) m/z = 157.9 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.56-1.82 (m, 1H), 1.85-2.09 (m, 1H), 2.47-2.61 (m, 1H), 2.73-2.86 (m, 1H), 2.91-3.06 (m, 1H), 3.38-3.54 (m, 2H), 3.55-3.74 (m, 2H), 4.25-4.47 (m, 2H)

Reference Example 156: Synthesis of 3-(3-oxiran-2-ylpropyl)-1,3-oxazolidin-2-one

[0345] By using 2-oxazolidinone (3 g) and 5-bromo-1-pentene (5.3 ml) as starting materials, the title compound (1.22 g) was obtained in the same manners as those of Reference Example 154, (1) and Reference Example 26, (2).
MS (ESI) m/z = 171.8 [M+H]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.37-1.59 (m, 1H), 1.60-1.84 (m, 3H), 2.50 (dd, J=4.83, 2.64Hz, 1H), 2.78 (d, J=4.83Hz, 1H), 2.89-3.02 (m, 1H), 3.27-3.38 (m, 2H), 3.51-3.64 (m, 2H), 4.24-4.41 (m, 2H)

Reference Example 157: Synthesis of benzyl 3-oxiran-2-ylpropionate

[0346] 

(1) 4-Pentenoic acid (15 g) was dissolved in toluene (100 ml), the solution was added with p-toluenesulfonic acid monohydrate (1.29 g) and benzyl alcohol (78 ml) under ice cooling, and the mixture was stirred under reflux by heating for 3.5 hours. The reaction mixture was left to cool, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 30:1 to 20:1) to obtain an ester compound (37.5 g).

(2) By using the compound obtained in (1) mentioned above (6.0 g) as a starting material, the title compound (6.3 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 229.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.67-2.11 (m, 2H), 2.41-2.61 (m, 3H), 2.68-2.79 (m, 1H), 2.89-3.06 (m, 1H), 5.13 (s, 2H), 7.28-7.43 (m, 5H)

Reference Example 158: Synthesis of 5-oxiran-2-ylpentanenitrile

[0347] By using 6-heptenenitrile (2.5 g) as a starting material, the title compound (2.91 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 148.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.42-1.86 (m, 6H), 2.32-2.44 (m, 2H), 2.48 (dd, J=5.05, 2.86Hz, 1H), 2.77 (dd, J=5.27,3.96Hz, 1H), 2.85-3.01 (m, 1H)

Reference Example 159: Synthesis of 2-[3-(benzyloxy)butyl]oxirane

[0348] 

(1) 5-Hexen-2-ol (2.9 g) was dissolved in dimethylformamide (55 ml), the solution was added portionwise with sodium hydride (1.06 g) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with benzyl chloride (4.0 m), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 20:1 to 10:1) to obtain a benzyl ether compound (5.16 g).

(2) By using the compound obtained in (1) mentioned above (5.09 g) as a starting material, the title compound (3.21 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 229.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.17-1.25 (m, 3H), 1.46-1.82 (m, 4H), 2.37-2.51 (m, 1H), 2.68-2.78 (m, 1H), 2.84-2.97 (m, 1H), 3.47-3.65 (m, 1H), 4.37-4.65 (m, 2H), 7.16-7.47 (m, 5H)

Reference Example 160: Synthesis of benzyl [3-[(2R)-oxiran-2-yl]propyl]carbamate

[0349] 

(1) 5-Bromo-1-pentene (25 g) was dissolved in dimethylformamide (120 ml), the solution was added with potassium phthalimide (34.2 g) under ice cooling, and the mixture was stirred at 60°C for 2 hours. The deposited solid was separated by filtration, and the filtrate was added with diethyl ether. Then, the mixture was washed successively with distilled water and saturated brine, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in ethanol (200 ml), the solution was added with hydrazine monohydrate (24.4 ml) under ice cooling, and the mixture was stirred at 60°C for 20 minutes. The reaction mixture was added with diluted hydrochloric acid under ice cooling and thereby made acidic, and the deposited solid was separated by filtration. The filtrate was concentrated under reduced pressure, the resulting residue was added with potassium hydroxide under ice cooling, thereby made basic, and extracted with chloroform, and the organic layer was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate (200 ml), the mixture was added with benzyl chloroformate (31.5 g) on an ice bath, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain a carbamate compound (9.13 g).

(2) By using the compound obtained in (1) mentioned above (9.10 g) as a starting material, a diol compound (9.39 g) was obtained in the same manner as that of Reference Example 2, (3).

(3) By using the compound obtained in (2) mentioned above (9.39 g) as a starting material, the title compound (9.38 g) was obtained in the same manner as that of Reference Example 1.
MS (ESI) m/z = 258.1 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.39-1.82 (m, 3H), 2.35-2.56 (m, 2H), 2.65-2.80 (m, 1H), 2.84-2.98 (m, 1H), 3.14-3.34 (m, 2H), 5.01-5.17 (m, 2H), 7.14-7.47 (m, 5H)

Reference Example 161: Synthesis of 1-(2-oxiran-2-ylethyl)pyridin-2(1H)-one

[0350] 

(1) 2-Hydroxypyridine (5 g) was dissolved in 1,4-dioxane (70 ml), the solution was added with 4-bromo-1-butene (5.87 ml) and cesium carbonate (17.1 g), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain an adduct compound (5.18 g).

(2) By using the compound obtained in (1) mentioned above (3.0 g) as a starting material, the title compound (479 mg) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 188.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.66-1.85 (m, 1H), 2.15-2.36 (m, 1H), 2.49 (dd, J=4.83, 2.64Hz, 1H), 2.79 (dd, J=4.83, 3.96Hz, 1H), 2.89-3.04 (m, 1H), 4.05-4.16 (m, 2H), 6.11-6.22 (m, 1H), 6.51-6.62 (m, 1H), 7.25-7.40 (m, 2H)

Reference Example 162: Synthesis of 1-(3-oxiran-2-ylpropyl)pyridin-2(1H)-one

[0351] 

(1) By using 5-bromo-1-pentene (5.07 ml) as a starting material, an adduct compound (3.79 g) was obtained in the same manner as that of Reference Example 161, (1).

(2) By using the compound obtained in (1) mentioned above (3.79 g) as a starting material, the title compound (4.06 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (ESI) m/z = 202.0 [M+Na]^+
1H-NMR (200MHz, CDCl₃) δ (ppm): 1.37-1.58 (m, 1H), 1.64-2.04 (m, 3H), 2.50 (dd, J=5.27, 2.64Hz, 1H), 2.76 (dd, J=4.83, 3.96Hz, 1H), 2.91-3.02 (m, 1H), 3.86-4.13 (m, 2H), 6.10-6.20 (m, 1H), 6.52-6.61 (m, 1H), 7.29-7.37 (m, 2H)

Reference Example 163: Synthesis of N-[1-(4-benzyloxy-3-methoxyphenyl)-ethyl]-N-ethylethane-1,2-diamine

[0352] 

(1) 1-(4-Hydroxy-3-methoxyphenyl)ethanone (1.66 g) was dissolved in acetone (100 ml), the solution was successively added with potassium carbonate (1.66 g) and benzyl bromide (1.4 ml), and the mixture was stirred at room temperature for 21 hours. The reaction mixture was concentrated under reduced pressure, the resulting the residue was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain a benzyl ether compound (1.74 g).

(2) By using the compound obtained in (1) mentioned above (1.74 g) as a starting material, the title compound (320 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (ESI) m/z = 329 [M+H]⁺

Reference Example 164: Synthesis of N-[1-(2,6-bisbenzyloxyphenyl)-ethyl]-N-ethylethane-1,2-diamine

[0353] By using 1-(2,6-di hydroxyphenyl)ethanone (1.53 g) as a starting material, the title compound (325 mg) was obtained in the same manners as those of Reference Example 163, (1), Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 405 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.89 (t, J=7.30Hz, 3H), 1.46 (d, J=7.07Hz, 3H), 2.45-2.60 (m, 4H), 2.63-2.73 (m, 2H), 4.67 (q, J=7.06Hz, 1H), 5.07 (s,4H), 6.62 (d, J=8.28Hz, 2H), 7.13 (t, J=8.28Hz, 1H), 7.31-7.47 (m, 10H)

Reference Example 165: Synthesis of N-[1-(4-ethoxy-3-piperidin-1-ylmethylphenyl)-ethyl]-N-ethylethane-1,2-diamine

[0354] By using 1-[4-ethoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone (520 mg) as a starting material, the title compound (44.3 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (FAB) m/z = 334 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.06Hz, 3H), 1.32 (d, J=6.58Hz, 3H), 1.40 (t, J=7.06Hz, 3H), 1.54-1.65 (m, 6H), 2.35-2.67 (m, 10H), 3.65 (s, 2H), 3.84 (q, J=6.82Hz, 1H), 4.01 (q, J=6.82Hz, 2H), 6.78 (d, J=8.28Hz, 1H), 7.15 (dd, J=2.19, 8.52Hz, 1H), 7.34 (d, J=1.95Hz, 1H)

Reference Example 166: Synthesis of 2-[5-[1-[(2-aminoethyl)ethylamino]ethyl]-2-methoxyphenyl] acetonitrile

[0355] By using 2-(5-acetyl-2-methoxyphenyl)acetonitrile (420 mg) as a starting material, the title compound (137 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (ESI) m/z = 262 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 1.02 (t, J=7.07Hz, 3H), 1.32 (d, J=6.82Hz, 3H), 2.37-2.69 (m, 6H), 3.68 (s, 2H), 3.83 (q, J=6.82Hz, 1H), 3.85 (s, 3H), 6.83 (d, J=5.12Hz, 1H), 7.28 (dd, J=2.19, 8.52Hz, 1H), 7.34 (d, J=1.95Hz, 1H)

Reference Example 167: Synthesis of N-ethyl-N-[1-(5-methylisoxazol-4-yl)ethyl]ethane-1,2-diamine

[0356] By using 1-(5-methylisoxazol-4-yl)ethanone (1.0 g) as a starting material, the title compound (412 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 198 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.14Hz, 3H), 1.31 (d, J=6.87Hz, 3H), 2.28-2.60 (m, 4H), 2.42 (s, 3H), 2.62-2.75 (m, 2H), 2.85 (q, J=6.86Hz, 1H), 8.12 (s, 1H)

Reference Example 168: Synthesis of N-[1-(4-ethoxy-3-morpholin-4-ylmethylphenyl)ethyl]-N-ethylethane-1,2-diamine

[0357] By using 1-[4-ethoxy-3-(morpholinomethyl)phenyl]ethanone (527 mg) as a starting material, the title compound (177 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (FAB) m/z = 336 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.01 (t, J=7.14Hz, 3H), 1.32 (d, J=6.59Hz, 3H), 1.41 (t, J=7.14Hz, 3H), 2.32-2.68 (m, 10H), 3.57 (s, 2H), 3.72 (t, J=4.67Hz, 4H), 3.83 (q, J=6.86Hz, 1H), 4.02 (q, J=6.86Hz, 2H), 6.79 (d, J=8.24Hz, 1H), 7.16 (dd, J=2.20, 8.24Hz, 1H), 7.32 (d, J=1.92Hz, 1H)

Reference Example 169: Synthesis of [5-[[1-[(2-aminoethyl)ethylamino]ethyl]thiophen-2-yl]acetonitrile

[0358] By using 2-(5-acetylthiophen-2-yl)acetonitrile (826 mg) as a starting material, the title compound (291 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (FAB) m/z = 238 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.06 (t, J=7.42Hz, 3H), 1.36 (d, J=6.87Hz, 3H), 2.37-2.60 (m, 4H), 2.64-2.82 (m, 2H), 3.85 (s, 2H), 4.08 (q, J=6.32Hz, 1H), 6.70 (dd, J=1.37, 3.57Hz, 1H), 6.86-6.89 (m, 1H)

Reference Example 170: Synthesis of N-ethyl-N-[1-(3-methylpyrazin-2-yl)ethyl]ethane-1,2-diamine

[0359] By using 1-(3-methylpyrazin-2-yl)ethanone (0.5 g) as a starting material, the title compound (245 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 209 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.04 (t, J=7.14Hz, 3H), 1.38 (d, J=6.59Hz, 3H), 2.39-2.71 (m, 6H), 2.71 (s, 3H), 4.28 (q, J=6.59Hz, 1H), 8.34 (dd, J=2.20, 4.89Hz, 2H)

Reference Example 171: Synthesis of N-ethyl-N-(1-pyridin-4-ylethyl)ethane-1,2-diamine

[0360] By using 1-(pyridin-4-yl)ethanone (2.0 g) as a starting material, the title compound (439 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (FAB) m/z = 194 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.14Hz, 3H), 1.34 (d, J=6.87Hz, 3H), 2.37-2.61 (m, 4H), 2.65-2.74 (m, 2H), 3.86 (q, J=6.87Hz, 1H), 7.30 (d, J=5.77Hz, 2H), 8.53 (dd, J=3.02, 4.67Hz, 2H)

Reference Example 172: Synthesis of N-ethyl-N-[1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

[0361] By using 1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethanone (0.5 g) as a starting material, the title compound (205 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (FAB) m/z = 225 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.15Hz, 3H), 1.25 (d, J=6.86Hz, 3H), 1.45 (t, J=7.14Hz, 3H), 2.27 (s, 3H), 2.35-2.51 (m, 4H), 2.59-2.72 (m, 2H), 3.89 (q, J=6.87Hz, 1H), 4.07 (q, J=7.14Hz, 2H), 7.17 (s, 1H)

Reference Example 173: Synthesis of N-[1-(2,4-dimethyloxazol-5-yl)ethyl]-N-ethylethane-1,2-diamine

[0362] By using 1-(2,4-dimethyloxazol-5-yl)ethanone (500 mg) as a starting material, the title compound (260 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 212 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.04 (t, J=7.1Hz, 3H), 1.37 (d, J=6.9Hz, 3H), 2.11 (s, 3H), 2.27-2.41 (m, 5H), 2.59-2.74 (m, 4H), 3.93 (q, J=6.9Hz, 1H)

Reference Example 174: Synthesis of N-[1-[3-(1H-tetrazol-1-yl)phenyl]ethyl]-N-ethylethane-1,2-diamine

[0363] By using 1-[3-(1H-tetrazol-1-yl)phenyl]ethanone (565 mg) as a starting material, the title compound (190 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (FAB) m/z = 261 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.05 (t, J=7.0Hz, 3H), 1.38 (d, J=6.6Hz, 3H), 2.46-2.75 (m, 6H), 3.97 (q, J=6.6Hz, 1H), 7.49-7.58 (m, 3H), 7.79 (s, 1H), 9.05 (s, 1H)

Reference Example 175: Synthesis of N-ethyl-N-[1-(1,3,5-trimethyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

[0364] By using 1-(1,3,5-trimethyl-1H-pyrazol-4-yl)ethanone (500 mg) as a starting material, the title compound (228 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (ESI) m/z = 225 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.95 (t, J=7.0Hz, 3H), 1.30 (d, J=6.9Hz, 3H), 2.23 (m, 6H), 2.46-2.71 (m, 6H), 3.66-3.71 (m, 4H)

Reference Example 176: Synthesis of N-ethyl-N-[1-(4-morpholinophenyl)ethyl]ethane-1,2-diamine

[0365] By using 1-(4-morpholinophenyl)ethanone (1.0 g) as a starting material, the title compound (178 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (FAB) m/z = 278 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.01 (t, J=7.1Hz, 3H), 1.30-1.38 (m, 3H), 2.34-2.67 (m, 6H), 3.13-3.17 (m, 4H), 3.79-3.88 (m, 5H), 6.86 (d, J=8.6Hz, 2H), 7.25 (d, J=8.6Hz, 2H)

Reference Example 177: Synthesis of N-ethyl-N-[1-[4-(morpholinosulfonyl)phenyl]ethyl]ethane-1,2-diamine

[0366] By using 1-[4-(morpholinosulfonyl)phenyl]ethanone (539 mg) as a starting material, the title compound (187 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (ESI) m/z = 342 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.1Hz, 3H), 1.36 (d, J=6.6Hz, 3H), 2.41-2.62 (m, 4H), 2.68 (t, J=6.0Hz, 2H), 2.99-3.02 (m, 4H), 3.74-3.77 (m, 4H), 3.93 (q, J=6.6Hz, 1H), 7.55 (d, J=8.2Hz, 2H), 7.69 (d, J=8.2Hz, 2H)

Reference Example 178: Synthesis of N-ethyl-N-[1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl]ethane-1,2-diamine

[0367] By using 1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethanone (500 mg) as a starting material, the title compound (73 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4). MS (FAB) m/z = 225 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.03 (t, J=7.1Hz, 3H), 1.28 (d, J=6.9Hz, 3H), 1.39 (t, J=7.2Hz, 3H), 2.26 (s, 3H), 2.36-2.52 (m, 4H), 2.63 (t, J=6.3Hz, 2H), 3.87 (q, J=6.9Hz, 1H), 4.09 (q, J=7.2Hz, 2H), 7.27 (s, 1H)

Reference Example 179: Synthesis of N-ethyl-N-[1-[4-methoxy-3-[(1-methyl-1H-tetrazol-5-ylthio)methyl]phenyl]ethyl]ethane-1,2-diamine

[0368] By using 1-[4-methoxy-3-[(1-methyl-1H-tetrazol-5-ylthio)methyl]phenyl]ethanone (500 mg) as a starting material, the title compound (267 mg) was obtained in the same manners as those of Reference Example 64, (1), Reference Example 63, (1) and Reference Example 54, (4).
MS (ESI) m/z = 351 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.00 (t, J=7.1Hz, 3H), 1.26 (d, J=6.6Hz, 3H), 2.33-2.65 (m, 6H), 3.77-3.82 (m, 4H), 3.85 (s, 3H), 4.53 (s, 2H), 6.82 (d, J=8.5Hz, 1H), 7.26-7.27 (m, 1H), 7.31 (d, J=1.9Hz, 1H)

Reference Example 180: Synthesis of 2-[4-[1-(2-aminoethylamino)ethyl]phenoxy]-N,N-diethylacetamide

[0369] By using 2-(4-acetylphenoxy)-N,N-diethylacetamide (250 mg), ethylenediamine (400 µl) and acetic acid (700 µl) as starting materials, the title compound (52.9 mg) was obtained in the same manner as that of Reference Example 64, (1).
MS (FAB) m/z = 294 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.14 (t, J=7.1Hz, 3H), 1.24 (t, J=7.1Hz, 3H), 1.34 (d, J=6.6Hz, 3H), 2.42-2.56 (m, 2H), 2.71 (t, J=6.1Hz, 2H), 3.38-3.46 (m, 4H), 3.70 (q, J=6.6Hz, 1H), 4.88 (s, 2H), 6.92 (d, J=8.7Hz, 2H), 7.26 (d, J=8.7Hz, 2H)

Reference Example 181: Synthesis of 2-[4-[1-(2-aminoethylamino)ethyl]phenoxy]-1-(pyrrolidin-1-yl)ethanone

[0370] By using 2-(4-acetylphenoxy)-1-(pyrrolidin-1-yl)ethanone (250 mg), ethylenediamine (400 µl) and acetic acid (700 µl) as starting materials, the title compound (163.8 mg) was obtained in the same manner as that of Reference Example 64, (1).
MS (FAB) m/z = 292 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.34 (d, J=6.6Hz, 3H), 1.86-2.04 (m, 4H), 2.42-2.55 (m, 2H), 2.70 (t, J=6.3Hz, 2H), 3.45-3.73 (m, 5H), 4.70 (s, 2H), 6.92 (d, J=8.7Hz, 2H), 7.25 (d, J=8.7Hz, 2H)

Reference Example 182: Synthesis of N-[1-[4-(1H-tetrazol-1-yl)phenyl]ethyl]ethane-1,2-diamine

[0371] By using 1-[4-(1H-tetrazol-1-yl)phenyl]ethanone (250 mg), ethylenediamine (400 µl) and acetic acid (700 µl) as starting materials, the title compound (60.5 mg) was obtained in the same manner as that of Reference Example 64, (1).
MS (FAB) m/z = 233 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.42 (d, J=6.5Hz, 3H), 2.55-2.72 (m, 2H), 2.83-2.92 (m, 2H), 3.90 (q, J=6.5Hz, 1H), 7.64 (d, J=8.5Hz, 2H), 7.84 (d, J=8.5Hz, 2H), 9.76 (s, 1H)

Reference Example 183: Synthesis of 4-[1-(2-aminoethylamino)ethyl]-2-methoxyphenol

[0372] 

(1) 1-(4-Hydroxy-3-methoxyphenyl)ethanone (1 g) was dissolved in dimethylformamide (5 ml), the solution was added with imidazole (1.3 g) and t-butyldimethylchlorosilane (1 g), and the mixture was stirred at room temperature for 4.5 hours. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1) to obtain 1-(4-t-butyldimethylsilyloxy-3-methoxyphenyl)ethanone (1.6 g).

(2) By using the compound obtained in (1) mentioned above (560 mg) as a starting material, the title compound (90.3 mg) was obtained in the same manner as that of Reference Example 96.
MS (ESI) m/z = 211 [M+H]^+
1 H-NMR (400MHz, CD₃OD) δ (ppm): 1.35 (d, J=6.82Hz, 3H), 2.42-2.57 (m, 2H), 2.70J=6.57Hz, 2H), 3.66 (q, J=6.82Hz, 1H), 3.85 (s, 3H), 6.73 (d, J=0.93Hz, 2H), 6.93 (s, 1H)

Reference Example 184: Synthesis of 6-[1-(2-aminoethylamino)ethyl]-3-(t-butyldimethylsilyloxy)-2-methylphenol

[0373] By using 1-(2,4-dihydroxy-3-methylphenyl)ethanone (1.0 g) as a starting material, the title compound (103 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 96.
MS (ESI) m/z = 325 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 0.08 (s, 6H), 1.02 (s, 9H), 1.38 (d, J=6.58Hz, 3H), 2.01 (s, 3H), 2.53-2.82 (m, 4H), 3.85 (q, J=6.82Hz, 1H), 6.25 (d, J=8.03Hz, 1H), 6.66 (d, J=8.04Hz, 1H)

Reference Example 185: Synthesis of 6-[1-(2-aminoethylamino)ethyl]-2,3-dimethoxyphenol

[0374] By using 1-(2-hydroxy-3,4-dimethoxyphenyl)ethanone (200 mg) as a starting material, the title compound (23.5 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 96.
MS (ESI) m/z = 241 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.40 (d, J=6.82Hz, 3H), 2.54-2.82 (m, 4H), 3.77 (s, 3H), 3.79 (s, 3H), 3.94 (q, J=6.82Hz, 1H), 6.44 (d, J=8.52Hz, 1H), 6.75 (d, J=8.76Hz, 1H)

Reference Example 186: Synthesis of 4-[1-(2-aminoethylamino)ethyl]-2-methoxymethylphenol

[0375] By using 1-[4-hydroxy-3-(methoxymethyl)phenyl]ethanone (250 mg) as a starting material, the title compound (72.9 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 96.
MS (ESI) m/z = 225 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.34 (d, J=6.57Hz, 3H), 2.40-2.54 (m, 2H), 2.68 (t, J=6.58Hz, 2H), 3.39 (s, 3H), 3.66 (q, J=6.58Hz, 1H), 4.48 (s, 2H), 6.75 (d, J=8.28Hz, 1H), 7.08 (dd, J=2.19, 8.28Hz, 1H), 7.19 (d, J=2.20Hz, 1H)

Reference Example 187: Synthesis of 2-[1-(2-aminoethylamino)ethyl]-4-methoxyphenol

[0376] By using 1-(2-hydroxy-5-methoxyphenyl)ethanone (363 mg) as a starting material, the title compound (224 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 96.
MS (ESI) m/z = 325 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.39 (d, J=6.82Hz, 3H), 2.51-2.58 (m, 2H), 2.62-2.79 (m, 2H), 3.70 (s, 3H), 3.89 (q, J=6.82Hz, 1H), 6.61-6.68 (m, 3H)

Reference Example 188: Synthesis of 2-[1-(2-aminoethylamino)ethyl]benzene-1,3-diol

[0377] By using 1-(2,6-dihydroxyphenyl)ethanone (329 mg) as a starting material, the title compound (93.6 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 96.
MS (ESI) m/z = 197 [M+H]^+
1H-NMR (400MHz, CD₃OD) δ (ppm): 1.37 (d, J=6.57Hz, 3H), 2.56-2.82 (m, 4H), 4.41 (q, J=6.82Hz, 1H), 6.20 (d, J=8.04Hz, 2H), 6.84 (t, J=8.04Hz, 1H)

Reference Example 189: Synthesis of 2-(3,4-dihydro-1H-isoquinolin-2-yl)ethylamine

[0378] By using 1,2,3,4-tetrahydroisoquinoline (335 mg) as a starting material, the title compound (458 mg) was obtained in the same manners as those of Reference Example 54, (3) and (4).
MS (FAB) m/z = 177 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.60 (t, J=5.86Hz, 2H), 2.75 (t, J=5.86Hz, 2H), 2.96 (q, J=6.35Hz, 4H), 3.64 (s, 2H), 6.99-7.04 (m, 1H), 7.07-7.15 (m, 3H)

Reference Example 190: Synthesis of (S)-N-[1-(2-methoxyphenyl)ethyl]-2-nitro-N-(4-oxobutyl)benzenesulfonamide

[0379] 

(1) (1S)-1-(2-Methoxyphenyl)ethanamine (2.45 g) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) was dissolved in dichloromethane (20 ml), the solution was added with ortho-nitrobenzenesulfonyl chloride (3.52 g) and triethylamine (2.64 ml) under ice cooling, and the mixture was stirred for 1 hour under ice cooling. The reaction mixture was added with 1 N hydrochloric acid and chloroform, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a protected compound (4.91 g) as a crude product.

(2) The compound obtained in (1) mentioned above (3.00 g) was dissolved in dimethylformamide (45 ml), the solution was added with 5-bromo-1-pentane (1.58 ml), sodium iodide (0.266 g) and potassium carbonate (2.46 g), and the mixture was stirred at 80°C for 4 hours and further stirred at 100°C for 3 hours. The reaction mixture was left to cool, and then added with distilled water, chloroform and saturated brine, the layers were separated, and then the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain N-pentenyl compound (2.32 g).

(3) The compound obtained in (2) mentioned above (567 mg) was dissolved in acetone/distilled water = 3/1 (11 ml), the solution was added with 4 wt% aqueous osmium tetraoxide (445 µl) and sodium periodate (1.05 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated brine and chloroform, the layers were separated, and then the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain the title compound (293 mg).
MS (ESI) m/z = 407 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.67-1.92 (m, 5H), 2.34-2.51 (m, 2H), 3.19-3.41 (m, 2H), 3.45 (s, 3H), 5.30 (q, J=7.2Hz, 1H), 6.67 (d, J=8.1Hz, 1H), 6.92 (t, J=7.5Hz, 1H), 7.19-7.25 (m, 1H), 7.37 (d, J=7.5Hz, 1H), 7.43-7.60 (m, 3H), 7.66 (d, J=8.1Hz, 1H), 9.64 (s, 1H)

Reference Example 191: Synthesis of (S)-4-[ethyl[1-(2-methoxyphenyl)ethyl]amino]butanoic acid

[0380] The compound obtained in Reference Example 190 (100 mg) was dissolved in t-butanol-distilled water-tetrahydrofuran (2.4:0.6:0.4, 3.4 ml), the solution was successively added with 2-methyl-2-butene (115 µl), sodium dihydrogenphosphate (38.4 mg) and 80% sodium chlorite (94.5 mg), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was added with 1 N hydrochloric acid, thereby adjusted to pH 2, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate, and the organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol = 10:1) to obtain the title compound (93.9 mg).
MS (ESI) m/z = 423 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.71 (d, J=7.14Hz, 3H), 1.73-1.96 (m, 2H), 2.21-2.48 (m, 2H), 3.20-3.49 (m, 2H), 3.45 (s, 3H), 5.32 (q, J=7.14Hz, 1H), 6.67 (d, J=8.25Hz, 1H), 6.87-6.94 (m, 1H), 7.18-7.26 (m, 1H), 7.34-7.40 (m, 1H), 7.41-7.62 (m, 3H), 7.67 (dd, J=1.38, 7.97Hz, 1H)

Reference Example 192: Synthesis of 2-[ethyl(4-hydroxybutyl)amino]-N,N-dimethylpropanamide

[0381] 

(1) 4-(t-Butyldimethylsilyloxy)-1-butanol (12.5 g) was dissolved in dichloromethane (250 ml), the solution was added with molecular sieves 4A (79 g) and pyridinium chlorochromate (15.8 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with diethyl ether (250 ml), and added with Florisil (79 g), and then the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 50:1) to obtain an aldehyde compound (2.98 g).

(2) Alanine methyl ester hydrochloride (350 mg) was added to chloroform, and the mixture was successively added with triethylamine (350 µl), the compound obtained in (1) mentioned above (1.01 g), and sodium triacetoxyborohydride (0.5 g). The mixture was stirred at room temperature for 19 hours, and then added with acetaldehyde (710 µl) and sodium triacetoxyborohydride (638 mg), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 50:1 to 15:1) to obtain an amine compound (233 mg).

(3) The compound obtained in (2) mentioned above (233 mg) was dissolved in methanol (4.7 ml), the solution was added with 1 N aqueous potassium hydroxide (1.47 ml), and the mixture was stirred at room temperature for 13 hours, and then further stirred at 40°C for 3.5 hours. The reaction mixture was left to cool to room temperature, added with 1 N hydrochloric acid, thereby adjusted to pH 7, and then concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran-distilled water (1:1, 4.48 ml), the solution was added with triethylamine (206 µl) and isobutyl chloroformate (107 µl) under ice cooling, and the mixture was stirred for 20 minutes. The reaction mixture was added with 50% aqueous dimethylamine (773 µl), and the mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 100:1 to 20:1) to obtain a dimethylamide compound (50.4 mg).

(4) The compound obtained in (3) mentioned above (50.4 mg) was dissolved in tetrahydrofuran (1.0 ml), the solution was added with a hydrogen fluoride/pyridine complex (11.9 µl), and the mixture was stirred at room temperature for 8.5 hours.
The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, and the layers were separated. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 100:1 to 5:1) to obtain the title compound (31.1 mg).
MS (CI) m/z = 217 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.07 (t, J=7.14Hz, 3H), 1.18 (d, J=6.87Hz, 3H), 1.48-1.64 (m, 4H), 2.42-2.70 (m, 4H), 2.95 (s, 3H), 3.13 (s, 3H), 3.56-3.62 (m, 2H), 3.85 (q, J=6.60Hz, 1H)

Reference Example 193: Synthesis of (S)-2-[ethyl[1-(2-methoxyphenyl)ethyl]amino]ethanol

[0382] 

(1) (1S)-1-(2-Methoxyphenyl)ethanamine (0.25 g) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) was dissolved in chloroform, the solution was added with 2-(t-butyldimethylsilyloxy)-acetaldehyde (0.35 ml) and sodium triacetoxyborohydride (0.42 g) under ice cooling, and the mixture was stirred for 1 hour under ice cooling and then stirred at room temperature for 2 hours. The reaction mixture was added with acetaldehyde (0.173 ml) and sodium triacetoxyborohydride (0.79 g), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol = 8:1) to obtain a tertiary amine compound (73.5 mg).

[0383] 

(2) The compound obtained in (1) mentioned above (73.5 mg) was dissolved in tetrahydrofuran (1.5 ml), the solution was added with a hydrogen fluoride-pyridine complex (55 µl), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol = 5:1) to obtain the title compound (44.2 mg).
MS (ESI) m/z = 224 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.95 (t, J=7.2Hz, 3H), 1.32 (d, J=6.9Hz, 3H), 2.53 (q, J=7.2Hz, 2H), 2.58-2.73 (m, 2H), 2.94 (br,1H), 3.43-3.60 (m, 2H), 3.84 (s, 3H), 4.42 (q, J=6.9Hz, 1H), 6.87-6.96 (m, 2H), 7.21-7.30 (m, 2H)

Reference Example 194: Synthesis of (S)-N-(1-(2-methoxyphenyl)ethyl)-1H-imidazole-1-carboxamide

[0384] (S)-1-(2-Methoxyphenyl)ethanamine (100 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) was dissolved in dimethylformamide (0.65 ml), the solution was added with N,N'-carbonyldiimidazole (321 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain the title compound (147 mg).
MS (ESI) m/z = 246 [M+H]⁺

Reference Example 195: Synthesis of (S)-2-[ethyl[1-(2-methoxyphenyl)ethyl]amino]acetic acid 2,2,2-trifluoroacetic acid salt

[0385] 

(1) The compound obtained in Reference Example 190, (1) (101 mg) was dissolved in dimethylformamide (2 ml), the solution was added with t-butyl bromoacetate (70.2 mg), potassium iodide (59.8 mg) and potassium carbonate (62.2 mg), and under an argon atmosphere, the mixture was stirred at 80°C for 20 hours, and then further stirred at 100°C for 2 days. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to obtain an ester compound (65.1 mg).

(2) The compound obtained in (1) mentioned above (152 mg) was dissolved in dimethylformamide (2 ml), the solution was added with thiophenol (172 µl) and potassium carbonate (233 mg), and the mixture was stirred at room temperature for 22 hours under an argon atmosphere. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to obtain a deprotected compound (86 mg).

(3) By using the compound obtained in (2) mentioned above (26.5 mg) as a starting material, a tertiary amine compound was obtained as a crude product in the same manner as that of Reference Example 193, (1). The resulting compound was dissolved in dichloromethane (1 ml), the solution was added with trifluoroacetic acid (0.5 ml), and then the reaction mixture was stirred at room temperature for 20 hours, and concentrated under reduced pressure to obtain the title compound (24.9 mg).
¹H-NMR (400MHz, CDCl₃) δ (ppm): 1.48 (t, J=7.3Hz, 3H), 1.71 (d, J=7.1Hz, 3H), 3.31 (q, J=7.3Hz, 2H), 3.79 (d, J=16.8Hz, 1H), 3.91 (d, J=16.8Hz, 1H), 4.03 (s, 3H), 4.85 (q, J=7.1Hz, 1H), 7.03 (d, J=8.5Hz, 1H), 7.10-7.13 (m, 1H), 7.24-7.26 (m, 1H), 7.46-7.52 (m, 1H)

Reference Example 196: Synthesis of (S)-N-[1-(2-methoxyphenyl)ethyl]-2-nitro-N-(4-oxopropyl)benzenesulfonamide

[0386] By using the compound obtained in Reference Example 190, (1) (336 mg) and 4-bromo-1-butene (504 µl) as starting materials, the title compound (104 mg) was obtained in the same manners as those of Reference Example 190, (2) and (3).
MS (ESI) m/z = 393 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.61 (t, J=7.2Hz, 3H), 2.36-2.47 (m, 1H), 2.68-2.79 (m, 1H), 3.52 (s, 3H), 3.61-3.67 (m, 2H), 5.41 (q, J=7.2Hz, 1H), 6.73 (d, J=8.1Hz, 1H), 6.91 (dt, J=7.5, 0.9Hz, 1H), 7.22-7.33 (m, 2H), 7.48-7.61 (m, 3H), 7.70 (dd, J=7.8, 1.2Hz, 1H), 9.57 (s, 1H)

Reference Example 197: Synthesis of (S)-2-amino-3-(4-methoxyphenyl)propan-1-ol

[0387] 

(1) Lithium aluminum hydride (512 mg) was suspended in ice-cooled tetrahydrofuran (15 ml) under an argon atmosphere, and the suspension was added with (S)-2-t-butoxycarbonylamino-3-(4-methoxyphenyl)propanoic acid (1.0 g). The mixture was stirred for 30 minutes, then warmed to room temperature, and further stirred for 3 hours. The reaction mixture was ice-cooled again, and successively added with distilled water (512 µl), 15% aqueous sodium hydroxide (512 µl) and distilled water (1.54 ml), and the mixture was stirred for 30 minutes, and filtered through Celite.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1 to 3:2) to obtain an alcohol compound (718 mg).

(2) The compound obtained in (1) mentioned above (718 mg) was dissolved in dioxane-methanol (3.5:1, 4.5 ml), the solution was added with a 4 N hydrochloric acid solution in dioxane (3.59 ml) under ice cooling, and the mixture was stirred for 1.5 hours, then warmed to room temperature, and stirred for 2 hours. The reaction mixture was added with diethyl ether-hexane (1:1, 14 ml), and the deposited solid was taken by filtration. The resulting filtration product was suspended in chloroform-methanol (10:1, 20 ml), and filtered through NH silica gel, and then the filtrate was concentrated under reduced pressure to obtain the title compound (315 mg).
MS (CI) m/z = 182 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.47 (dd, J=8.49, 13.64Hz, 1H), 2.70 (dd, J=5.36, 13.64Hz, 1H), 3.04-3.12 (m, 1H), 3.37 (dd, J=7.31, 10.72Hz, 1H), 3.63 (dd, J=3.90, 10.47Hz, 1H), 3.80 (s, 3H), 6.84-6.88 (m, 2H), 7.04-7.14 (m, 2H)

Reference Example 198: Synthesis of 2-hydroxy-2-(4-methoxyphenyl)ethylamine

[0388] 2-Amino-4'-methoxyacetophenone hydrochloride (500 mg) was dissolved in methanol (10 ml), the solution was added with sodium borohydride (188 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with sodium borohydride (188 mg), and further stirred for 30 minutes. The reaction mixture was added with 5 N aqueous sodium hydroxide (1 ml), the mixture was stirred for 10 minutes, and then added with chloroform, and the layers were separated. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain the title compound (240 mg).
MS (FAB) m/z = 168 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.80 (dd, J=7.8, 12.7Hz, 1H), 2.98 (dd, J=4.1, 7.8Hz, 1H), 3.81 (s, 3H), 4.59 (dd, J=4.1, 7.8Hz, 1H), 6.89 (m, 2H), 7.28 (m, 2H)

Reference Example 199: Synthesis of 2-(benzyloxy)ethyl oxiran-2-ylethylcarbamate

[0389] 

(1) Allyl isocyanate (2.38 g) was dissolved in toluene (29 ml), the solution was added with benzyloxyethanol (4.1 ml) and 1,4-diazabicyclo[2.2.2]octane (963 mg), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1 to 5:1) to obtain 2-(benzyloxy)ethyl allylcarbamate (5.1 g).

(2) By using the compound obtained in (1) mentioned above (5.1 g) as a starting material, the title compound (4.86 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (FAB) m/z = 252 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.60 (dd, J=2.47, 4.67Hz, 1H), 2.78 (t, J=4.40Hz, 1H), 3.07-3.14 (m, 1H), 3.26 (ddd, J=5.22, 6.32, 4.8Hz, 1H), 3.55-3.65 (m, 1H), 3.66 (t, J=4.67Hz, 2H), 4.26 (t, J=4.67Hz, 2H), 4.56 (s, 2H), 7.22-7.40 (m, 5H)

Reference Example 200: Synthesis of propargyl oxiran-2-ylmethylcarbamate

[0390] By using allyl isocyanate (2.40 g) and propargyl alcohol (1.7 ml) as starting materials, the title compound (3.35 g) was obtained in the same manners as those of Reference Example 199, (1) and Reference Example 26, (2).
MS (FAB) m/z = 155 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.49 (t, J=2.47Hz, 1H), 2.62 (dd, J=2.75, 4.67Hz, 1H), 2.81 (t, J=4.67Hz, 1H), 3.09-3.17 (m, 1H), 3.23-3.35 (m, 1H), 3.58-3.70 (m, 1H), 4.69 (d, J=2.20Hz, 2H), 5.00-5.20 (m, 1H)

Reference Example 201: Synthesis of 2-(6-t-butyldimethylsilyloxyhexyl)oxirane

[0391] By using 7-octen-1-ol (5.0 g) as a starting material, the title compound (7.9 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 259 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.05 (s, 6H), 0.89 (s, 9H), 1.29-1.58 (m, 10H), 2.46 (dd, J=2.68, 5.12Hz, 1H), 2.75 (dd, J=4.14, 5.11Hz, 1H), 2.87-2.95 (m, 1H), 3.60 (t, J=6.82Hz, 2H)

Reference Example 202: Synthesis of 2-(5-t-butyldimethylsilyloxypentyl)oxirane

[0392] By using 6-hepten-1-ol (5.0 g) as a starting material, the title compound (8.74 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 245 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.05 (s, 6H), 0.89 (s, 9H), 1.34-1.58 (m, 8H), 2.47 (dd, J=2.68, 5.11Hz, 1H), 2.75 (dd, J=4.14, 5.11Hz, 1H), 2.87-2.94 (m, 1H), 3.61 (t, J=6.58Hz, 2H)

[0393] Reference Example 203: Synthesis of 2-[(1-triethylsilyloxycyclohexyl)methyl]oxirane

(1) 1-Allylcyclohexanol (5.0 g) was dissolved in dichloromethane (50 ml), the solution was added with 2,6-lutidine (4.98 ml) and triethylsilyl trifluoromethanesulfonate (8.06 ml) under ice cooling, and the mixture was stirred for 2 hours, and then at room temperature for 12 hours. The reaction mixture was added with 10% aqueous citric acid and hexane, the layers were separated, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain a triethylsilyl compound (8.9 g).

(2) By using the compound obtained in (1) mentioned above (8.9 g) as a starting material, the title compound (8.52 g) was obtained in the same manner as that of Reference Example 26, (2).
¹H-NMR (400MHz, CDCl₃) δ (ppm): 0.61 (q, J=7.80Hz, 6H), 0.96 (t, J=7.04Hz, 9H), 1.29-1.45 (m, 4H), 1.49-1.83 (m, 8H), 2.46 (dd, J=2.68, 5.11Hz, 1H), 2.78 (t, J=4.14Hz, 1H), 3.08-3.14 (m, 1H)

Reference Example 204: Synthesis of 2-(2-triethylsilyloxy-2-phenylpropyl)oxirane

[0394] By using 2-phenyl-4-penten-2-ol (2.5 g) as a starting material, the title compound (1.63 g) was obtained in the same manners as those of Reference Example 203, (1) and Reference Example 26, (2).
¹H-NMR (400MHz, CDCl₃) δ (ppm): 0.54-0.66 (m, 6H), 0.90-0.98 (m, 9H), 1.70-1.76 (m, 3H), 1.81-1.91 (m, 1H), 1.94-2.10 (m, 1H), 2.13-2.41 (m, 1H), 2.53-2.65 (m, 1H), 2.71-3.07 (m, 1H), 7.20-7.49 (m, 5H)

Reference Example 205: Synthesis of 2-(2-triethylsilyloxy-2-methylbutyl)oxirane

[0395] By using 3-methyl-5-hexen-3-ol (2.5 g) as a starting material, the title compound (4.23 g) was obtained in the same manners as those of Reference Example 203, (1) and Reference Example 26, (2).
¹H-NMR (400MHz, CDCl₃) δ (ppm): 0.05-0.63 (m, 6H), 0.85-0.99 (m, 12H), 1.23-1.31 (m, 3H), 1.51-1.72 (m, 4H), 2.43-2.47 (m, 1H), 2.75-2.80 (m, 1H), 3.03-3.12 (m, 1H)

Reference Example 206: Synthesis of 2-O-t-butyldimethylsilyl-1-(oxiran-2-yl)propan-2-ol

[0396] 

(1) By using 4-penten-2-ol (5.0 g) as a starting material, 2-O-t-butyldimethylsilyl-4-penten-2-ol (8.4 g) was obtained in the same manner as that of Reference Example 183, (1).

(2) By using the compound obtained in (1) mentioned above (6.0 g) as a starting material, the title compound (6.13 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (FAB) m/z = 252 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.06-0.14 (m, 6H), 0.90 and 0.91 (s, 9H), 1.19 and 1.23 (d, J=6.04Hz, 3H), 1.45-1.61 (m, 1H), 1.65-1.81 (m, 1H), 2.45-2.54 (m, 1H), 2.74-2.84 (m, 1H), 2.89-3.08 (m, 1H), 3.88-4.12 (m, 1H)

Reference Example 207: Synthesis of 1,2-di-O-t-butyldimethylsilyl-4-(oxiran-2-yl)butane-1,2-diol

[0397] By using 5-hexene-1,2-diol (5.0 g) as a starting material, the title compound (8.00 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (ESI) m/z = 361 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.07 (s, 6H), 0.08 (s, 6H), 0.89 (s, 9H), 0.91 (s, 9H), 1.45-1.85 (m, 4H), 2.45-2.51 (m, 1H), 2.76 (t, J=4.40Hz, 1H), 2.89-2.97 (m, 1H), 3.36-3.45 (m, 1H), 3.50-3.58 (m, 1H), 3.65-3.76 (m, 1H)

Reference Example 208: Synthesis of allyl (S)-(oxiran-2-ylmethyl)carbamate

[0398] 

(1) By using (S)-3-amino-1,2-propanediol (2.9 g) as a starting material, a carbamate compound (1.15 g) was obtained in the same manner as that of Reference Example 30, (1).

(2) The compound obtained in (1) mentioned above (1.15 g) was dissolved in chloroform, the solution was added with pyridine (1.9 ml) and p-toluenesulfonyl chloride (1.50 g), and the mixture was stirred at room temperature for 4.5 hours.
The reaction mixture was added with p-toluenesulfonyl chloride (125 mg), and the mixture was further stirred at room temperature for 1.5 hours. The reaction mixture was added with 2 N hydrochloric acid, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in methanol (15 ml), the solution was added with a 1 N solution of sodium methoxide in methanol (15.2 ml), and the mixture was stirred for 1.5 hours under ice cooling.
The reaction mixture was added with 20% aqueous ammonium chloride, and methanol was evaporated under reduced pressure. The concentrate was added with ethyl acetate, the layers were separated, and the organic layer was washed successively with saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1 to 3:1) to obtain the title compound (670 mg).
MS (FAB) m/z = 158 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 2.62 (dd, J=2.75, 4.67Hz, 1H), 2.80 (dd, J=3.85, 4.67Hz, 1H), 3.05-3.20 (m, 1H), 3.20-3.35 (m, 1H), 3.50-3.70 (m, 1H), 4.58 (d, J=5.77Hz, 2H), 4.82-5.07 (m, 1H), 5.17-5.40 (m, 2H), 5.83-6.02 (m, 1H)

Reference Example 209: Synthesis of (S)-2-allyloxirane

[0399] By using (S)-epichlorohydrin (5.0 g) as a starting material, the title compound (1.05 g) was obtained according to the method described in the literature (Journal of American Chemical Society, 2004, vol. 126, p.2495).
MS (EI) m/z = 84 [M]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.27-2.40 (m, 2H), 2.52 (dd, J=2.68, 4.87Hz, 1H), 2.77 (dd, J=4.14, 4.87Hz, 1H), 2.97-3.03 (m, 1H), 5.09-5.21 (m, 2H), 5.78-5.89 (m, 1H)

Reference Example 210: Synthesis of 2-(2-t-butyldimethylsilyloxybenzyl)oxirane

[0400] By using 2-allylphenol (4.0 g) as a starting material, the title compound (6.3 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (EI) m/z = 265 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.25 (s, 3H), 0.26 (s, 3H), 1.02 (s, 9H), 2.53 (dd, J=2.68, 4.87Hz, 1H), 2.72-2.79 (m, 2H), 2.98 (dd, J=5.36, 14.37Hz, 1H), 3.17-3.23 (m, 1H), 6.81 (dd, J=1.22, 8.28Hz, 1H), 6.88-6.94 (m, 1H), 7.09-7.15 (m, 1H), 7.21 (dd, J=1.71, 7.55Hz, 1H)

Reference Example 211: Synthesis of allyl 2-[(oxiran-2-yl)ethyl]carbamate

[0401] 

(1) Acetyl chloride (2.6 ml) was added to methanol (240 ml) under ice cooling, the mixture was stirred for 10 minutes, and then added with (S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoic acid (30 g), and the mixture was gradually warmed from ice cooling temperature to room temperature, and stirred for 16.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and methanol was evaporated under reduced pressure. The concentrate was added with ethyl acetate, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was added with dichloromethane to dissolve the residue, and the mixture was added with molecular sieves 4A (140 g) and pyridinium chlorochromate (30.7 g). The mixture was stirred at room temperature for 2.5 hours, and then further added with pyridinium chlorochromate (21.1 g), and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added with diethyl ether and Florisil, and filtered through Celite under reduced pressure. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 3:1 to 1:2) to obtain 4-(benzyloxycarbonylamino)-2-oxobutanoic acid methyl ester (17 g).

(2) A suspension of lithium borohydride (4.51 g) in diethyl ether (350 ml) was added with a solution of the compound obtained in (1) mentioned above (16.5 g) in diethyl ether (150 ml) under ice cooling, and then the mixture was stirred at room temperature for 20 hours. The reaction mixture was added with 20% aqueous ammonium chloride and concentrated hydrochloric acid (20 ml), and the mixture was stirred at room temperature for 20 minutes, and then made alkaline with sodium hydrogencarbonate. The organic layer and the aqueous layer were separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=70:1 to 10:1) to obtain a 1,2-diol compound (11.3 g).

(3) The compound obtained in (2) mentioned above (11.6 g) was dissolved in methanol (120 m), the solution was added with 10% palladium-carbon (580 mg), and the mixture was stirred at room temperature for 16 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 4-amino-1,2-butanediol (6.10 g).

(4) By using the compound obtained in (3) mentioned above (3.0 g) as a starting material, a carbamate compound (3.40 g) was obtained in the same manner as that of Reference Example 30, (1).

(5) By using the compound obtained in (4) mentioned above (3.40 g) as a starting material, the title compound (1.65 g) was obtained in the same manner as that of Reference Example 208, (2).
MS (ESI) m/z = 172 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 1.54-1.68 (m, 1H), 1.88-2.04 (m, 1H), 2.53 (dd, J=2.75, 4.67Hz, 1H), 2.79 (t, J=4.95Hz, 1H), 2.95-3.05 (m, 1H), 3.28-3.46 (m, 2H), 4.57 (d, J=5.22Hz, 2H), 5.04 (brs, 1H), 5.17-5.28 (m, 2H), 5.84-6.01 (m, 1H)

Reference Example 212: Synthesis of 2-methoxy-4-(oxiran-2-ylmethyl)phenyl acetate

[0402] By using 4-allyl-2-methoxyphenyl acetate (5.0 g) as a starting material, the title compound (5.2 g) was obtained in the same manner as that of Reference Example 26, (2).
MS (GC) m/z = 222 [M]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.32 (s, 3H), 2.56 (dd, J=2.68, 4.88Hz, 1H), 2.81-2.90 (m, 3H), 3.14-3.18 (m, 1H), 3.84 (s, 3H), 6.82-6.87 (m, 2H), 6.97 (d, J=8.08Hz, 1H)

Reference Example 213: Synthesis of 2-(2-t-butyldimethylsilyloxy-2-phenylethyl)oxirane

[0403] By using 1-phenyl-3-buten-1-ol (2.5 g) as a starting material, the title compound (4.43 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 278 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): -0.15 - -0.11 (m, 3H), 0.02-0.08 (m, 3H), 0.87-0.92 (m, 9H), 1.61-1.81 (m, 1H), 1.90-2.10 (m, 1H), 2.41-2.48 (m, 1H), 2.65-2.81 (m, 1H), 2.82-3.19 (m, 1H), 4.83-4.93 (m, 1H), 7.21-7.37 (m, 1H)

Reference Example 214: Synthesis of 2-(2-t-butyldimethylsilyloxyhexyl)oxirane

[0404] By using 1-octen-4-ol (10.0 g) as a starting material, the title compound (18.25 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 259 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.04-0.10 (m, 6H), 0.86-0.94 (m, 12H), 1.22-1.38 (m, 4H), 1.45-1.76 (m, 4H), 2.44-2.52 (m, 1H), 2.74-2.82 (m, 1H), 3.00-3.08 (m, 1H), 3.82-3.92 (m, 1H)

Reference Example 215: Synthesis of 2-(2-t-butyldimethylsilyloxy-3-methylbutyl)oxirane

[0405] By using 2-methyl-5-hexen-3-ol (10.0 g) as a starting material, the title compound (18.6 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 244 [M]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.04-0.11 (m, 6H), 0.83-0.93 (m, 15H), 1.45-1.66 (m, 2H), 1.74-1.86 (m, 1H), 2.43-2.54 (m, 1H), 2.74-2.83 (m, 1H), 2.98-3.06 (m, 1H), 3.61-3.76 (m, 1H)

Reference Example 216: Synthesis of 2-(2-t-butyldimethylsilyloxypentyl)oxirane

[0406] By using 1-hepten-4-ol (10.0 g) as a starting material, the title compound (16.1 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (CI) m/z = 245 [M+H]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 0.04-0.09 (m, 6H), 0.86-0.94 (m, 12H), 1.25-1.76 (m, 6H), 2.43-2.52 (m, 1H), 2.74-2.83 (m, 1H), 2.99-3.08 (m, 1H), 3.81-3.92 (m, 1H)

Reference Example 217: Synthesis of 1-O-t-butyldimethylsilyl-4-methoxy-2-(oxiran-2-ylmethyl)phenol

[0407] By using 2-allyl-4-methoxyphenol (1.0 g) as a starting material, the title compound (600 mg) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (GC) m/z = 294 [M]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.31-2.35 (m, 1H), 2.48-2.58 (m, 2H), 2.67-2.75 (m, 1H), 2.95-3.01 (m, 1H), 3.55 (s, 3H), 6.46 (dd, J=3.43, 8.08Hz, 1H), 6.52 (d, J=8.08Hz, 1H), 6.58 (d, J=3.43Hz, 1H)

Reference Example 218: Synthesis of 1-O-t-butyldimethylsilyl-1-(4-methoxyphenyl)-2-(oxiran-2-yl)ethanol

[0408] By using 1-(4-methoxyphenyl)-3-buten-1-ol (4.0 g) as a starting material, the title compound (5.4 g) was obtained in the same manners as those of Reference Example 183, (1) and Reference Example 26, (2).
MS (GC) m/z = 293 [M-15]^+
1H-NMR (400MHz, CDCl₃) δ (ppm): 2.31-2.35 (m, 1H), 2.48-2.58 (m, 2H), 2.67-2.75 (m, 1H), 2.95-3.01 (m, 1H), 3.55 (s, 3H), 6.46 (dd, J=3.43, 8.08Hz, 1H), 6.52 (d, J=8.08Hz, 1H), 6.58 (d, J=3.43Hz, 1H)

Reference Example 219: Synthesis of benzyl 4-(oxiran-2-yl)butanate

[0409] By using 5-pentenoic acid (5.0 g) as a starting material, the title compound (10.0 g) was obtained in the same manners as those of Reference Example 25, (1) and Reference Example 26, (2).
MS (GC) m/z = 220 [M]⁺

Reference Example 220: Synthesis of 2-(2-methoxyphenyl)propan-1-amine

[0410] 

(1) 2-(2-Methoxyphenyl)acetonitrile (2.0 g) was dissolved in anhydrous tetrahydrofuran (40 ml), and the solution was added with a 1 M solution of lithium hexamethyldisilazide in hexane (14.3 ml) at -78°C under an argon atmosphere. The mixture was stirred at -78°C for 1 hour, and then added with iodomethane (0.89 ml), and the mixture was stirred at -78°C for 1.5 hours, and stirred overnight with warming to room temperature. The reaction mixture was added with 0.2 N hydrochloric acid, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 24:1 to 3:1) to obtain a methyl compound (2.13 g).

(2) The compound obtained in (1) mentioned above (1.00 g) was dissolved in anhydrous tetrahydrofuran (30 ml), the solution was added with a 2 M solution of a borane/dimethyl sulfide complex in tetrahydrofuran (4.31 ml) under an argon atmosphere, and the mixture was stirred for 3 hours under reflux by heating. The reaction mixture was added with concentrated hydrochloric acid, and the mixture was concentrated under reduced pressure. The resulting residue was dissolved in chloroform, and the solution was dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain an amine hydrochloride (1.39 g).

(3) The compound obtained in (2) mentioned above (636 mg) was dissolved in dichloromethane (10 ml), then adsorbed to NH silica gel (Fuji Silysia), and then eluted with ethyl acetate. The elute was concentrated under reduced pressure, and the precipitates deposited during the concentration was taken by filtration to obtain the title compound (99.5 mg).
MS(EI): m/z= 165 [M]^+
1H-NMR (400 MHz, CDCl₃) δ (ppm): 1.40 (d, J=7.06 Hz, 3H), 3.08 (dd, J=7.79, 12.42 Hz, 1H), 3.19 (dd, J=6.82, 12.66 Hz, 1H), 3.48-3.59 (m, 1H), 3.85 (s, 3H), 6.88 (d, J=8.28Hz, 1H), 6.89-6.94 (m, 1H), 7.17-7.26 (m, 2H)

Syntheses of Examples 1 to 6

[0411] Preparation methods of the compounds represented by the formula (A) having R and R' defined in the examples are shown below.

[0412] 

Example 1: Synthesis of the compound of the formula (A) wherein R = methyl and R' = triethylsilyl

[0413] 

(1) (9S)-9,2',4"-O-Tis(triethylsilyl)-9-dihydro-6-O-methylerythromycin A (200 g) was dissolved in chloroform (400 ml), the solution was added with 90% lead tetraacetate (90.2 g) under ice cooling, and the mixture was stirred for 10 minutes. The mixture was further added successively with a solution of 2-methyl-2-butene (51.3 g) in tetrahydrofuran (800 ml), t-butyl alcohol (400 ml) and an aqueous solution (400 ml) of sodium chlorite (33.1 g), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (700 ml), the mixture was stirred and then added with ethyl acetate (1000 ml), and the layers were separated. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate (500 ml) and saturated brine (500 ml), then dried over anhydrous magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure to obtain a 10-carboxy compound (218.9 g).

[0414] 

(2) A solution of the compound obtained in (1) mentioned above (218.9 g) in toluene (500 ml) was concentrated under reduced pressure, the resulting residue was dissolved in chloroform (500 ml), and the solution was added with triethylamine (28.1 ml). Then, the mixture was added dropwise with isobutyl chloroformate (25.0 g) under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. Then, the mixture was added with 50% aqueous hydroxylamine (12.1 g) under ice cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride (500 ml), the layers were separated, and the organic layer was washed with saturated brine (500 ml), then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a 10-hydroxamic acid compound (219.9 g).

[0415] 

(3) A solution of the compound obtained in (2) mentioned above (219.9 g) in toluene (500 ml) was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (800 ml). The solution was successively added with triethylamine (77.0 ml) and p-toluenesulfonyl chloride (38.4 g), the mixture was stirred at room temperature for 40 minutes, and then further added with an aqueous solution (260 ml) of lithium hydroxide (38.4 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride (500 ml), thereby neutralized, and then concentrated under reduced pressure, the resulting residue was added with chloroform (1000 ml), and the layers were separated. The organic layer was washed with saturated aqueous sodium hydrogencarbonate (500 ml), then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 40:1:0.1 to 15:1:0.1) to obtain the title compound (44.3 g).
MS (ESI) m/z = 993.8 [M+H]^+
1H-NMR (500MHz, CDCl₃) δ (ppm): 0.51-0.70 (m,18H), 0.84-1.00 (m, J=7.84, 7.84Hz, 30H), 1.06-1.12 (m, 6H), 1.13-1.17 (m,7H), 1.22 (d, J=6.50Hz, 3H), 1.24 (d, J=6.88Hz, 3H), 1.30 (s, 3H), 1.30-1.35 (m, 1H), 1.42 (dd, J=14.72, 4.78Hz, 1H), 1.55-1.72 (m, 3H), 2.15-2.19 (m, 1H), 2.18 (s, 6H), 2.31-2.38 (m, 1H), 2.43-2.52 (m, 1H), 2.52-2.60 (m, 1H), 3.12 (dd, J=9.75, 7.07Hz, 1H), 3.18 (d, J=9.17Hz, 1H), 3.28 (s, 3H), 3.29 (s, 3H), 3.32-3.43 (m, 2H), 3.51-3.60 (m, 1H), 3.72 (d, J=7.65Hz, 1H), 3.83-3.88 (m, 1H), 4.19-4.29 (m, 1H), 4.43 (d, J=7.26Hz, 1H), 4.85 (d, J=4.59Hz, 1H)

Example 2: Synthesis of the compound of the formula (A) wherein R = hydrogen atom and R' = triethylsilyl

[0416] 

(1) By using (9S)-9,2',4"-O-tris(triethylsilyl)-9-dihydroerythromycin A (100 g) as a starting material, a 10-carboxy compound (53.4 g) was obtained in the same manner as that of Example 1, (1).

[0417] 

(2) The compound obtained in (1) mentioned above (53 g) was dissolved in tetrahydrofuran (700 ml), and the solution was added with triethylamine (8.0 ml). Then, the mixture was added dropwise with isobutyl chloroformate (7.0 ml) under ice cooling, and then the mixture was stirred for 30 minutes. Then, the reaction mixture was bubbled with ammonia gas for 1 hour under ice cooling. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a 10-amide compound (36.1 g).

[0418] 

(3) The compound obtained in (2) mentioned above (17.3 g) was dissolved in ethyl acetate (340 ml), the solution was added with iodobenzenediacetate (10.2 g), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (90 ml). The solution was added with an aqueous solution (30 ml) of lithium hydroxide (3.3 g), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was added with saturated ammonium chloride, and the mixture was concentrated under reduced pressure. The residue was added with ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, and then dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0.1) to obtain the title compound (6.8 g).
MS (ESI) m/z = 979.9 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.49-0.76 (m,18H), 0.84-1.04 (m,30H), 1.03-1.37 (m,23H), 1.37-1.72 (m, 3H), 1.77-1.93 (m, 1H), 2.01-2.18 (m, 1H), 2.19 (s, 6H), 2.32 (d, J=15.23Hz, 1H), 2.38-2.56 (m, 2H), 3.13-3.29 (m, 3H), 3.30 (s, 3H), 3.37-3.54 (m, 1H), 3.56 (d, J=6.84Hz, 1H), 3.62 (s, 1H), 3.64-3.80 (m, 1H), 4.13 (d, J=4.97Hz, 1H), 4.17-4.30 (m, 1H), 4.60 (d, J=6.68Hz, 1H), 4.64 (d, J=4.35Hz, 1H)

Example 3: Synthesis of the compound of the formula (A) wherein R = hydrogen atom and R' = benzyl

[0419] 

(1) (9S)-2'-O-Acetyl-9-dihydroerythromycin A (8.51 g) obtained by the method described in the literature (Journal of Organic Chemistry, 1982, vol. 47, p.5019) was dissolved in tetrahydrofuran (85 ml), the solution was added with benzyl bromide (1.37 ml), and the mixture was stirred at room temperature for 3 minutes. Then, the mixture was added with potassium hydroxide (3.1 g), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was added with saturated aqueous ammonium chloride, and the aqueous layer was extracted with ethyl acetate. The resulting organic layer was successively washed with saturated aqueous ammonium chloride, distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a 9-O-benzyl compound (8.6 g).

[0420] 

(2) The compound obtained in (1) mentioned above (8.6 g) was dissolved in methanol (500 ml), and the solution was stirred for 8 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 40:1:0.1 to 30:1:0.1) to obtain a deacetylated compound (5.54 g).

[0421] 

(3) The compound obtained in (2) mentioned above (5.54 g) was dissolved in dimethylformamide (70 ml), and the solution was successively added with imidazole (3.4 g) and triethylchlorosilane (2.8 ml). The reaction mixture was stirred at room temperature for 63 hours, and then successively added with imidazole (850 mg) and triethylchlorosilane (0.7 ml), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous ammonium chloride, distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (acetone:hexane = 40:1 to 20:1) to obtain (9S)-9-O-benzyl-2',4"-O-bis(triethylsilyl)-9-dihydroerythromycin A (5.8 g).

[0422] 

(4) By using the compound obtained in (3) mentioned above (2.0 g) as a starting material, the title compound (264 mg) was obtained in the same manner as that of Example 1.
MS (ESI) m/z = 955.9 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.45-1.42 (m, 60H), 1.49-1.90 (m, 4H), 2.08-2.55 (m, 3H), 2.18 (s, 6H), 2.63-2.82 (m, 1H), 3.10-3.34 (m, 2H), 3.29 (s, 3H), 3.34-3.50 (m, 2H), 3.52-3.87 (m, 3H), 4.04-4.35 (m, 2H), 4.45-4.82 (m, 3H), 7.12-7.45 (m, 5H)

Example 4: Synthesis of the compound of the formula (A) wherein R = hydrogen atom and R'= 2-(N-benzyloxycarbonyl)aminoethyl

[0423] 

(1) By using (9S)-2'-O-acetyl-9-dihydroerythromycin A (10 g) and 2-bromoethylamine hydrobromide (3.95 g) as starting materials, a 9-O-(2-aminoethyl) compound (4.8 g) was obtained in the same manner as that of Example 3, (1).

[0424] 

(2) The compound obtained in (1) mentioned above (4.7 g) was dissolved in chloroform, the solution was successively added with an aqueous solution (25 ml) of sodium hydrogencarbonate (961 mg) and benzyl chloroformate (0.9 ml), and the mixture was stirred at room temperature for 1 hour. The layers of the reaction mixture were separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an N-benzyloxycarbonyl compound (4.9 g).

[0425] 

(3) By using the compound obtained in (2) mentioned above (4.9 g) as a starting material, the title compound (313 mg) was obtained in the same manners as those of Example 3, (2), (3), and Example 1.
MS (ESI) m/z = 1042.9 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.46-0.71 (m, 18H), 0.80-1.88 (m, 46H), 2.04-2.31 (m, 2H), 2.17 (s, 6H), 2.34-2.52 (m, 2H), 2.55-2.69 (m, 1H), 2.94-3.85 (m, 10H), 3.27 (s, 3H), 4.09-4.29 (m, 2H), 4.45-4.76 (m, 2H), 5.01-5.15 (m, 2H), 7.18-7.40 (m, 5H)

Example 5: Synthesis of the compound of the formula (A) wherein R = hydrogen atom and R' = 2-benzyloxyethyl

[0426] By using (9S)-2'-O-acetyl-9-dihydroerythromycin A (10 g) and benzyl 2-bromoethyl ether (4.73 g) as starting materials, the title compound (321 mg) was obtained in the same manners as those of Example 3, (1), (2), (3) and Example 1.
MS (ESI) m/z = 1000.0 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.49-0.70 (m, 18H), 0.79-1.86 (m, 46H), 2.09-2.22 (m, 1H), 2.17 (s, 6H), 2.24-2.38 (m, 1H), 2.38-2.55 (m, 2H), 3.10-3.37 (m, 4H), 3.31 (s, 3H), 3.42-3.81 (m, 5H), 3.85-3.94 (m, 1H), 4.04-4.26 (m, 2H), 4.46-4.60 (m, 2H), 4.66-4.85 (m, 2H), 7.13-7.41 (m, 5H)

Example 6: Synthesis of the compound of the formula (A) wherein R = propargyl and R' = triethylsilyl

[0427] By using (9S)-9,2',4"-O-tris(triethylsilyl)-9-dihydro-6-O-propargylerythromycin A (48.4 g) as a starting material, the title compound (13.8 g) was obtained in the same manner as that of Example 1.
MS (ESI) m/z = 1017.9 [M+H]⁺

Syntheses of Examples 7 to 108

[0428] Preparation methods of the compounds of the formula (B) having R defined in Table 1 are shown below.

[Table 1-1]

[0429] 

Table 1

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
7		719.2	(300 MHz) : 0.82 (d, J=6.99 Hz, 6 H) 0.90 (t, J=7.38 Hz, 3 H) 1.06 - 1.28 (m, 5 H) 1.11 (d, J=7.31 Hz, 3 H) 1.17 (d, J=7.46 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.50 - 1.91 (m, 5 H) 2.11 - 2.54 (m, 7 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.95 (m, 2 H) 3.01 (t, J=8.63 Hz, 1 H) 3.18 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.39 - 3.52 (m, 2 H) 3.71 (d, J=8.24 Hz, 1 H) 4.02 - 4.10 (m, 1 H) 4.17 (d, J=4.35 Hz, 1 H) 4.40 (d, J=7.15 Hz, 1 H) 4.61 - 4.68 (m, 1 H) 4.95 (d, J=4.51 Hz, 1 H)
8	H	691.5	(500 MHz) : 0.81 - 0.89 (m, 6 H) 1.10 (d, J=7.65 Hz, 3 H) 1.10 - 1.29 (m, 5 H) 1.18 (d, J=7.65 Hz, 3 H) 1.25 (s, 3 H) 1.30 (d, J=8.12 Hz, 3 H) 1.34 (s, 3 H) 1.53 - 1.58 (m, 1 H) 1.64 - 1.73 (m, 1 H) 1.85 - 1.94 (m, 1 H) 2.17 - 2.60 (m, 16 H) 2.76 - 2.83 (m, 1 H) 2.84 - 2.92 (m, 1 H) 3.02 (t, J=9.94 Hz, 1 H) 3.21 - 3.25 (m, 1 H) 3.26 (s, 3 H) 3.34 (s, 3 H) 3.46 - 3.55 (m, 2 H) 3.73 (d, J=7.65 Hz, 1 H) 3.75 - 3.86 (m, 1 H) 4.03 - 4.09 (m, 1 H) 4.15 (d, J=3.82 Hz, 1 H) 4.36 - 4.40 (m, 1 H) 4.42 (d, J=6.88 Hz, 1 H) 4.88 (d, J=4.59 Hz, 1 H)
9		811.5	(300 MHz) : 0.80 - 0.88 (m, 6 H) 1.10 (d, J=7.15 Hz, 3 H) 1.10 - 1.22 (m, 2 H) 1.16 (d, J=7.31 Hz, 3 H) 1.20 - 1.26 (m, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.06 Hz, 3 H) 1.33 (s, 3 H) 1.54 (dd, J=15.31, 4.90 Hz, 1 H) 1.63 - 1.72 (m, 1 H) 1.81 - 1.93 (m, 1 H) 2.17 - 2.55 (m, 7 H) 2.30 (s, 6 H) 2.33 (s, 3 H) 2.76 - 2.86 (m, 1 H) 2.90 (d, J=13.99 Hz, 1 H) 3.01 (t, J=9.71 Hz, 1 H) 3.17 - 3.25 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.40 - 3.52 (m, 2 H) 3.53 - 3.70 (m, 2 H) 3.71 (d, J=7.93 Hz, 1 H) 4.06 (dd, J=9.17, 6.37 Hz, 1 H) 4.15 (d, J=4.04 Hz, 1 H) 4.40 (d, J=6.84 Hz, 1 H) 4.53 (s, 2 H) 4.93 (d, J=4.82 Hz, 1 H) 4.98 (s, 1 H) 7.25 - 7.39 (m, 5 H)
10		719.3

[0430] 

[Table 1-2]

11		735.3	(500 MHz) : 0.85 (d, 6 H) 1.11 (d, J=7.65 Hz, 3 H) 1.12 - 1.35 (m, 2 H) 1.18 (d, J=7.65 Hz, 2 H) 1.24 (d, J=6.12 Hz, 3 H) 1.25 (s, 3 H) 1.30 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.52 - 1.71 (m, 2 H) 1.84 - 1.91 (m, 1 H) 2.21 - 2.54 (m, 6 H) 2.30 (s, 6 H) 2.35 (s, 3 H) 2.79 - 2.91 (m, 2 H) 3.02 (t, J=9.94 Hz, 1 H) 3.20 - 3.24 (m, 1 H) 3.25 (s, 3 H) 3.34 (s, 3 H) 3.36 (s, 3 H) 3.43 - 3.52 (m, 3 H) 3.57 (dd, J=9.94, 6.12 Hz, 1 H) 3.72 (d, J=7.65 Hz, 1 H) 4.03 - 4.10 (m, 1 H) 4.12 - 4.16 (m, 1 H) 4.41 (d, J=7.65 Hz, 1 H) 4.90 - 4.95 (m, 2 H)
12		705.4	(300 MHz) : 0.81 - 0.91 (m, 6 H) 1.06 - 1.23 (m, 2 H) 1.11 (d, J=7.31 Hz, 3 H) 1.16 (d, J=7.46 Hz, 3 H) 1.19 - 1.27 (m, 9 H) 1.29 (d, J=6.22 Hz, 3 H) 1.32 (s, 3 H) 1.55 (dd, J=15.15, 4.90 Hz, 1 H) 1.60 - 1.70 (m, 1 H) 1.90 (s, 1 H) 2.08 - 2.21 (m, 1 H) 2.21 - 2.42 (m, 4 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.45 - 2.54 (m, 2 H) 2.70 - 2.81 (m, 1 H) 2.89 (d, J=14.77 Hz, 1 H) 3.02 (t, J=8.39 Hz, 1 H) 3.17 - 3.25 (m, 1 H) 3.26 (s, 3 H) 3.34 (s, 3 H) 3.38 - 3.57 (m, 2 H) 3.72 (d, J=7.77 Hz, 1 H) 3.99 - 4.11 (m, 1 H) 4.13 (s, 1 H) 4.42 (d, J=7.15 Hz, 1 H) 4.86 (s, 1 H) 4.90 (d, J=4.51 Hz, 1 H)
13		733.4	(300 MHz) : 0.82 (d, J=6.99 Hz, 6 H) 0.91 (t, J=7.07 Hz, 3 H) 1.10 (d, J=7.46 Hz, 3 H) 1.11 - 1.91 (m, 15 H) 1.16 (d, J=7.31 Hz, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 2.06 - 2.54 (m, 7 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.74 - 2.85 (m, 1 H) 2.88 - 2.96 (m, 1 H) 3.01 (t, J=9.87 Hz, 1 H) 3.18 - 3.25 (m, 1 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.37 - 3.53 (m, 2 H) 3.71 (d, J=8.24 Hz, 1 H) 4.01 - 4.11 (m, 1 H) 4.17 (d, J=5.28 Hz, 1 H) 4.39 (d, J=7.15 Hz, 1 H) 4.69 - 4.77 (m, 1 H) 4.95 (d, J=4.97 Hz, 1 H)
14		733.5	(300 MHz) : 0.92 (t, J=7.23 Hz, 3 H) 0.95 - 1.79 (m, 27 H) 1.13 (d, J=7.31 Hz, 3 H) 1.29 (s, 3 H) 2.06 - 2.39 (m, 6 H) 2.24 (s, 3 H) 2.31 (s, 6 H) 2.45 - 2.85 (m, 3 H) 3.01 (t, J=9.64 Hz, 1 H) 3.21 - 3.41 (m, 8 H) 3.48 - 3.60 (m, 1 H) 3.82 (d, J=6.84 Hz, 1 H) 3.96 - 4.07 (m, 1 H) 4.27 - 4.34 (m, 1 H) 4.53 (d, J=7.62 Hz, 1 H) 4.66 (d, J=4.97 Hz, 1 H) 4.86 - 5.00 (m, 1 H)
15		747.5	(300 MHz) : 0.82 (d, J=6.84 Hz, 6 H) 0.89 (t, J=6.84 Hz, 3 H) 1.04 - 1.37 (m, 6 H) 1.10 (d, J=7.46 Hz, 3 H) 1.16 (d, J=7.46 Hz, 3 H) 1.21 - 1.25 (m, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.37 Hz, 3 H) 1.33 (s, 3 H) 1.48 - 1.59 (m, 1 H) 1.59 - 1.93 (m, 3 H) 2.07 - 2.20 (m, 1 H) 2.21 - 2.42 (m, 4 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.41 - 2.54 (m, 2 H) 2.80 (dd, J=7.46, 5.44 Hz, 1 H) 2.91 (d, J=16.16 Hz, 1 H) 3.01 (t, J=9.56 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.38 - 3.52 (m, 2 H) 3.71 (d, J=8.08 Hz, 1 H) 4.00 - 4.12 (m, 1 H) 4.17 (d, J=5.28 Hz, 1 H) 4.39 (d, J=7.31 Hz, 1 H) 4.71 (s, 1 H) 4.95 (d, J=4.35 Hz, 1 H)
16		811.5	(300 MHz) : 0.95 (d, J=6.99 Hz, 3 H) 1.00 (d, J=7.31 Hz, 3 H) 1.01 - 1.23 (m, 2 H) 1.08 - 1.18 (m, 6 H) 1.17 - 1.27 (m, 9 H) 1.29 (s, 3 H) 1.47 - 1.81 (m, 3 H) 1.92 - 2.99 (m, 9 H) 2.23 (s, 3 H) 2.29 (s, 6 H) 3.19 - 3.29 (m, 1 H) 3.30 (s, 3 H) 3.35 (s, 3 H) 3.42 - 3.58 (m, 2 H) 3.64 (t, J=4.97 Hz, 2 H) 3.80 (d, J=6.68 Hz, 1 H) 3.89 - 4.09 (m, 1 H) 4.36 (s, 1 H) 4.45 - 4.52 (m, 2 H) 4.52 (s, 2 H) 5.20 (s, 1 H) 7.27 - 7.39 (m, 5 H)
17		854.6	(300 MHz) : 0.78 - 0.90 (m, 6 H) 1.05 - 1.16 (m, 6 H) 1.12 - 1.22 (m, 2 H) 1.20 - 1.24 (m, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.37 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.60 - 1.71 (m, 1 H) 1.87 (s, 1 H) 2.18 - 2.39 (m, 5 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.40 - 2.54 (m, 2 H) 2.73 - 2.84 (m, 1 H) 2.91 - 3.01 (m, 1 H) 3.01 (t, J=9.87 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.34 - 3.56 (m, 4 H) 3.70 (d, J=8.08 Hz, 1 H) 3.98 - 4.14 (m, 2 H) 4.40 (d, J=7.31 Hz, 1 H) 4.85 (s, 1 H) 4.90 (d, J=4.82 Hz, 1 H) 5.05 (s, 1 H) 5.09 (s, 2 H) 7.28 - 7.39 (m, 5 H)
18		854.5	(300 MHz) : 0.88 - 0.99 (m, 6 H) 1.02 - 1.23 (m, 2 H) 1.07 (d, J=7.15 Hz, 3 H) 1.13 (d, J=7.46 Hz, 3 H) 1.18 - 1.30 (m, 12 H) 1.47 - 1.71 (m, 2 H) 1.80 - 2.63 (m, 7 H) 2.16 (s, 3 H) 2.27 (s, 6 H) 2.76 (t, J=10.26 Hz, 1 H) 2.93 - 3.10 (m, 2 H) 3.15 - 3.70 (m, 5 H) 3.27 (s, 3 H) 3.37 (s, 3 H) 3.77 (d, J=6.37 Hz, 1 H) 3.94 - 4.06 (m, 1 H) 4.39 (d, J=5.60 Hz, 1 H) 4.50 (s, 1 H) 4.56 (d, J=7.46 Hz, 1 H) 4.90 - 5.16 (m, 2 H) 5.37 - 5.50 (m, 1 H) 7.03 (s, 1 H) 7.27 - 7.40 (m, 5 H)
19		770.6	(300 MHz) : 0.80 - 0.87 (m, 6 H) 0.92 (d, J=7.31 Hz, 3 H) 1.08 (d, J=7.46 Hz, 3 H) 1.12 - 1.17 (m, 1 H) 1.18 - 125 (m, 1 H) 120 - 1.24 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.49 (dd, J=15.39, 4.97 Hz, 1 H) 1.62 - 1.73 (m, 1 H) 1.86 (s, 1 H) 2.19 - 2.36 (m, 5 H) 2.30 (s, 6 H) 2.40 (s, 3 H) 2.42 - 2.54 (m, 2 H) 2.64 - 2.75 (m, 1 H) 2.93 - 3.08 (m, 2 H) 3.16 - 3.26 (m, 1 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.39 - 3.54 (m, 2 H) 3.68 (d, J=7.93 Hz, 1 H) 3.97 - 4.08 (m, 3 H) 4.09 - 4.21 (m, 1 H) 4.38 (d, J=6.99 Hz, 1 H) 4.85 (d, J=4.51 Hz, 1 H) 4.99 (s, 1 H) 6.10 (t, J=2.10 Hz, 2 H) 6.63 (t, J=2.10 Hz, 2 H)

[0431] 

[Table 1-3]

20		770.5	(300 MHz) : 0.79 - 0.88 (m, 6 H) 0.92 (d, J=5.91 Hz, 3 H) 1.08 (d, J=7.46 Hz, 3 H) 1.12 - 1.18 (m, 1 H) 1.19 - 1.25 (m, 1 H) 1.19 - 1.25 (m, 6 H) 1.28 (d, J=6.06 Hz, 3 H) 1.33 (s, 3 H) 1.45 - 1.54 (m, 1 H) 1.61 - 1.73 (m, 1 H) 1.86 (s, 1 H) 2.19 - 2.36 (m, 5 H) 2.31 (s, 6 H) 2.40 (s, 3 H) 2.43 - 2.57 (m, 2 H) 2.66 - 2.75 (m, 1 H) 2.94 - 3.08 (m, 2 H) 3.16 - 3.26 (m, 1 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.39 - 3.51 (m, 2 H) 3.68 (d, J=7.93 Hz, 1 H) 3.97 - 4.19 (m, 4 H) 4.38 (d, J=6.99 Hz, 1 H) 4.85 (d, J=4.20 Hz, 1 H) 5.00 (s, 1 H) 6.10 (t, J=2.41 Hz, 2 H) 6.63 (t, J=2.10 Hz, 2 H)
21		748.5	(300 MHz) : 0.80 - 0.90 (m, 6 H) 1.12 (d, 3 H) 1.11 - 1.24 (m, 2 H) 1.17 (d, J=7.31 Hz, 3 H) 1.21 - 1.28 (m, 3 H) 1.25 (s, 3 H) 1.30 (d, J=6.22 Hz, 3 H) 1.34 (s, 3 H) 1.50 - 1.56 (m, 1 H) 1.60 - 1.72 (m, 1 H) 1.81 - 1.96 (m, 1 H) 2.13 - 2.57 (m, 9 H) 2.24 (s, 6 H) 2.30 (s, 6 H) 2.39 (s, 3 H) 2.80 (dd, J=6.61, 5.21 Hz, 1 H) 2.89 (d, J=15.39 Hz, 1 H) 3.02 (t, J=9.87 Hz, 1 H) 3.18 - 3.24 (m, 1 H) 3.25 (s, 3 H) 3.34 (s, 3 H) 3.38 - 3.56 (m, 2 H) 3.72 (d, J=7.62 Hz, 1 H) 4.07 (dd, J=9.71, 6.45 Hz, 1 H) 4.17 (d, J=5.60 Hz, 1 H) 4.41 (d, J=7.46 Hz, 1 H) 4.86 - 4.92 (m, 1 H) 4.94 (d, J=4.35 Hz, 1 H)
22		790.8	(300 MHz) : 0.79 - 0.87 (m, 6 H) 1.11 (d, J=7.15 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.18 (d, J=7.62 Hz, 3 H) 1.21 - 1.25 (m, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.49 - 1.56 (m, 1 H) 1.66 (d, J=13.21 Hz, 1 H) 1.87 (s, 1 H) 2.19 - 2.62 (m, 13 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.83 (m, 1 H) 2.88 (d, J=15.39 Hz, 1 H) 2.96 - 3.07 (m, 1 H) 3.15 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.46 (t, 2 H) 3.65 (t, J=5.05 Hz, 4 H) 3.71 (d, J=8.24 Hz, 1 H) 4.06 (dd, J=9.25, 6.14 Hz, 1 H) 4.12 (d, J=4.20 Hz, 1 H) 4.39 (d, J=7.31 Hz, 1 H) 4.93 (d, J=4.51 Hz, 1 H) 4.98 (s, 1 H)
23		918.8	(500 MHz) : 0.78 - 0.86 (m, 6 H) 1.04 - 1.11 (m, 6 H) 1.19 - 1.33 (m, 2 H) 1.22 (d, J=6.12 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.47 - 1.91 (m, 5 H) 2.05 - 2.40 (m, 15 H) 2.40 - 2.56 (m, 2 H) 2.70 - 2.78 (m, 1 H) 2.82 - 2.92 (m, 1 H) 3.01 (t, J=9.94 Hz, 1 H) 3.18 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.33 - 3.52 (m, 3 H) 3.58 (s, 2 H) 3.69 (d, J=8.41 Hz, 1 H) 3.98 - 4.12 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.67 - 4.80 (m, 1 H) 4.86 (d, J=4.59 Hz, 1 H) 5.64 - 5.87 (m, 1 H) 6.44 - 6.49 (m, 1 H) 6.67 (d, J=3.82 Hz, 1 H) 7.16 (d, J=7.65 Hz, 1 H) 7.33 - 7.38 (m, 1 H) 7.44 - 7.47 (m, 1 H) 7.55 - 7.60 (m, 2 H)
24		918.7	(500 MHz) : 0.75 - 0.88 (m, 6 H) 1.03 - 1.11 (m, 6 H) 1.10 - 1.21 (m. 2 H) 1.22 (d, J=6,1 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, 1 H) 1.58 - 1.91 (m, 4 H) 2.07 - 2.15 (m, 1 H) 2.18 - 2.37 (m, 4 H) 2.26 - 2.34 (m, 9 H) 2.38 - 2.54 (m, 2 H) 2.67 - 2.80 (m, 1 H) 2.82 - 2.92 (m, 1 H) 2.96 - 3.05 (m, 2 H) 3.22 (s, 3 H) 3.18 - 3.21 (m, 1 H) 3.26 - 3.42 (m, 2 H) 3.31 (s, 3 H) 3.42 - 3.52 (m, 1 H) 3.57 (s, 2 H) 3.69 (d, J=8.41 Hz, 1 H) 3.97 - 4.12 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.72 (s, 1 H) 4.86 (d, J=4.59 Hz, 1 H) 5.64 - 5.97 (m, 1 H) 6.44 - 6.48 (m, 1 H) 6.67 (d, J=3.82 Hz, 1 H) 7.16 (d, J=7.65 Hz, 1 H) 7.35 (t, J=8.03 Hz, 1 H) 7.46 (d, J=1.53 Hz, 1 H) 7.55 - 7.60 (m, 2 H)
25		893.5	(300 MHz) : 0.76 - 0.89 (m, 6 H) 1.05 - 1.16 (m, 6 H) 1.13 - 1.21 (m, 2 H) 1.23 (d, J=6.06 Hz, 3 H) 1.26 (s, 3 H) 1.30 (d, J=6.37 Hz, 3 H) 1.32 (s, 3 H) 1.46 - 1.97 (m, 5 H) 2.06 - 2.35 (m, 4 H) 2.29 (s, 6 H) 2.32 (s, 3 H) 2.38 (d, J=15.54 Hz, 1 H) 2.42 - 2.55 (m, 2 H) 2.71 - 2.84 (m, 1 H) 2.88 (d, J=13.99 Hz, 1 H) 2.96 - 3.12 (m, 2 H) 3.16 - 3.24 (m, 1 H) 3.24 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.56 (m, 3 H) 3.71 (d, J=8.08 Hz, 1 H) 3.95 (s, 2 H) 3.99 - 4.17 (m, 2 H) 4.40 (d, J=7.15 Hz, 1 H) 4.75 (s, 1 H) 4.89 (d,J=4.66 Hz, 1 H) 6.59 (s, 1 H) 7.29 - 7.40 (m, 1 H) 7.51 - 7.65 (m, 2 H) 7.79 (d, J=7.93 Hz, 1 H)
26		918.6	(300 MHz) : 0.75 - 0.88 (m, 6 H) 1.03 - 1.12 (m, 6 H) 1.10 - 1.22 (m, 2 H) 1.23 (d, J=6.06 Hz, 3 H) 1.25 (s, 3 H) 1.30 (d, J=6.37 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.23, 4.82 Hz, 1 H) 1.66 (d, J=11.19 Hz, 1 H) 1.71 - 1.93 (m, 3 H) 2.02 - 2.14 (m, 1 H) 2.16 - 2.29 (m, 3 H) 2.27 - 2.32 (m, 9 H) 2.36 (d, J=15.54 Hz, 1 H) 2.39 - 2.54 (m, 2 H) 2.71 (dd, J=7.38, 5.52 Hz, 1 H) 2.85 (d, J=14.61 Hz, 1 H) 2.94 - 3.10 (m, 2 H) 3.19 (d, J=7.15 Hz, 1 H) 3.23 (s, 3 H) 3.25 - 3.52 (m, 3 H) 3.32 (s, 3 H) 3.69 (d, J=8.08 Hz, 1 H) 3.77 (s, 2 H) 3.95 - 4.13 (m, 2 H) 4.39 (d, J=7.31 Hz, 1 H) 4.63 (s, 1 H) 4.88 (d, J=4.51 Hz, 1 H) 5.78 (s, 1 H) 6.48 (dd, J=3.42, 1.87 Hz, 1 H) 6.57 (dd, J=3.34, 0.70 Hz, 1 H) 7.29 - 7.39 (m, 3 H) 7.52 - 7.56 (m, 1 H) 7.64 - 7.71 (m, 1 H)

[0432] 

[Table 1-4]

27		918.6	(300 MHz) : 0.76 - 0.89 (m, 6 H) 1.04 - 1.11 (m, J=7.31 Hz, 6 H) 1.10 - 1.22 (m, 2 H) 1.18 - 1.26 (m, 6 H) 1.29 (d, J=6.22 Hz, 3 H) 1.32 (s, 3 H) 1.49 (dd, J=15.31, 4.74 Hz, 1 H) 1.60 - 1.94 (m, 4 H) 2.04 - 2.40 (m, 5 H) 2.29 (s, 6 H) 2.33 (s, 3 H) 2.41 - 2.54 (m, 2 H) 2.70 - 2.79 (m, 1 H) 2.89 (d, J=14.46 Hz, 1 H) 2.94 - 3.10 (m, 2 H) 3.17 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.32 - 3.52 (m, 3 H) 3.56 (s, 2 H) 3.69 (d, J=7.93 Hz, 1 H) 3.97 - 4.13 (m, 2 H) 4.39 (d, J=7.15 Hz, 1 H) 4.75 (s, 1 H) 4.86 (d, J=4.35 Hz, 1 H) 5.83 (s, 1 H) 6.47 (dd, J=3.34, 1.79 Hz, 1 H) 6.65 (d, J=3.42 Hz, 1 H) 7.27 - 7.34 (m, 2 H) 7.43 - 7.49 (m, 1 H) 7.65 (d, J=8.24 Hz, 2 H)
28		929.6	(300 MHz) : 0.76 - 0.91 (m, 6 H) 1.02 - 1.17 (m, 6 H) 1.11 - 1.22 (m, 2 H) 1.20 - 1.27 (m, 3 H) 1.24 (s, 3 H) 1.30 (d, J=6.53 Hz, 3 H) 1.32 (s, 3 H) 1.51 (dd, J=15.23, 4.66 Hz, 1 H) 1.59 - 1.97 (m, 4 H) 2.07 - 2.38 (m, 4 H) 2.30 (s, 6 H) 2.32 (s, 3 H) 2.38 - 2.56 (m, 2 H) 2.68 - 2.81 (m, 1 H) 2.88 (d, J=15.70 Hz, 1 H) 2.94 - 3.10 (m, 2 H) 3.13 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.27 - 3.55 (m, 3 H) 3.32 (s, 3 H) 3.65 (s, 2 H) 3.70 (d, J=7.93 Hz, 1 H) 3.93 - 4.15 (m, 2 H) 4.39 (d, J=7.15 Hz, 1 H) 4.75 (s, 1 H) 4.87 (d, J=4.66 Hz, 1 H) 5.87 (s, 1 H) 7.20 - 7.27 (m, 1 H) 7.31 - 7.39 (m, 1 H) 7.47 (t, J=7.46 Hz, 1 H) 7.70 - 7.79 (m, 2 H) 7.85 - 7.98 (m, 2 H) 8.69 (d, J=4.66 Hz, 1 H)
29		929.6	(300 MHz) : 0.76 - 0.92 (m, 6 H) 1.04 - 1.13 (m, 6 H) 1.10 - 1.23 (m, 2 H) 1.20 - 1.26 (m, 3 H) 1.23 - 1.26 (m, 3 H) 1.30 (d, J=6.68 Hz, 3 H) 1.32 (s, 3 H) 1.50 (dd, J=15.08, 4.82 Hz, 1 H) 1.60 - 1.96 (m, 4 H) 2.07 - 2.39 (m, 4 H) 2.29 (s, 6 H) 2.32 (s, 3 H) 2.39 - 2.55 (m, 2 H) 2.68 - 2.81 (m, 1 H) 2.87 (d, J=16.63 Hz, 1 H) 2.93 - 3.08 (m, 2 H) 3.15 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.30 - 3.55 (m, 3 H) 3.63 (s, 2 H) 3.70 (d, J=7.93 Hz, 1 H) 3.93 - 4.17 (m, 2 H) 4.40 (d, J=7.31 Hz, 1 H) 4.78 (s, 1 H) 4.86 (d, J=4.35 Hz, 1 H) 5.95 (s, 1 H) 7.29 - 7.41 (m, 2 H) 7.41 - 7.57 (m, 3 H) 7.84 - 7.95 (m, 1 H) 8.55 - 8.64 (m, 1 H) 8.85 (d, J=2.18 Hz, 1 H)
30		932.6	(300 MHz) : 0.78 - 0.85 (m, 6 H) 1.06 - 1.12 (m, 6 H) 1.11 - 1.35 (m, 8 H) 1.17 (d, J=7.62 Hz, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.46 - 2.08 (m, 5 H) 2.08 - 2.52 (m, 7 H) 2.27 (s, 3 H) 2.29 (s, 6 H) 2.34 - 2.37 (m, 3 H) 2.75 - 2.88 (m, 1 H) 2.91 - 3.05 (m, 2 H) 3.17 - 3.57 (m, 5 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.66 - 3.76 (m, 3 H) 4.00 - 4.09 (m, 1 H) 4.13 - 4.19 (m, 1 H) 4.39 (d, J=7.46 Hz, 1 H) 4.65 - 4.74 (m, 1 H) 4.90 - 4.94 (m, 1 H) 6.43 - 6.48 (m, 1 H) 6.66 (dd, J=3.34, 0.70 Hz, 1 H) 7.11 - 7.17 (m, 1 H) 7.33 (t, J=7.85 Hz, 1 H) 7.44 - 7.46 (m, 1 H) 7.53 - 7.59 (m, 2 H)
31		904.5	(300 MHz) : 0.74 - 0.87 (m, 6 H) 0.93 (d, J=7.15 Hz, 3 H) 1.04 (d, J=8.08 Hz, 3 H) 1.04 - 1.21 (m, 2 H) 1.22 (d, J=6.22 Hz, 3 H) 1.25 (s, 3 H) 1.28 (d, J=6.37 Hz, 3 H) 1.30 (s, 3 H) 1.43 - 1.71 (m, 2 H) 1.76 - 1.92 (m, 1 H) 2.06 - 2.73 (m, 9 H) 2.25 - 2.33 (m, 9 H) 2.81 - 3.07 (m, 2 H) 3.14 - 3.26 (m, 1 H) 3.20 (s, 3 H) 3.27 - 3.37 (m, 1 H) 3.31 (s, 3 H) 3.38 - 3.52 (m, 1 H) 3.59 (s, 2 H) 3.67 (d, J=7.31 Hz, 1 H) 3.95 - 4.13 (m, 2 H) 4.38 (d, J=7.15 Hz, 1 H) 4.76 (s, 1 H) 4.82 (d, J=4.35 Hz, 1 H) 5.86 (s, 1 H) 6.47 (dd, J=3.42, 1.87 Hz, 1 H) 6.68 (d, J=3.89 Hz, 1 H) 7.14 (d, J=8.08 Hz, 1 H) 7.37 (t, J=7.54 Hz, 1 H) 7.43 - 7.48 (m, 1 H) 7.51 - 7.64 (m, 2 H)
32		932.6	(300 MHz) : 0.78 - 0.85 (m, 6 H) 1.06 - 1.34 (m, 14 H) 1.29 (d, J=6.22 Hz, 3 H) 1.32 (s, 3 H) 1.36 - 1.73 (m, 6 H) 1.79 - 1.90 (m, 1 H) 2.04 - 2.13 (m, 1 H) 2.18 - 2.52 (m, 6 H) 2.29 (s, 9 H) 2.71 - 2.81 (m, 1 H) 2.83 - 2.92 (m, 1 H) 2.95 - 3.06 (m, 1 H) 3.16 - 3.52 (m, 5 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.59 (s, 2 H) 3.70 (d, J=8.24 Hz, 1 H) 4.00 - 4.15 (m, 2 H) 4.39 (d, J=7.15 Hz, 1 H) 4.63 - 4.72 (m, 1 H) 4.91 (d, J=4.20 Hz, 1 H) 5.46 - 5.54 (m, 1 H) 6.48 (dd, J=3.34, 1.79 Hz, 1 H) 6.68 (d, J=3.42 Hz, 1 H) 7.15 (d, J=7.77 Hz, 1 H) 7.37 (t, J=7.69 Hz, 1 H) 7.48 (d, J=1.09 Hz, 1 H) 7.56 - 7.63 (m, 2 H)
33		918.5	(300 MHz) : 0.83 (d, J=6.99 Hz, 6 H) 1.09 (d, J=7.46 Hz, 3 H) 1.13 (d, J=7.46 Hz, 3 H) 1.23 (d, J=6.06 Hz, 3 H) 1.22 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.32 (s, 3 H) 1.46 - 1.70 (m, 2 H) 1.81 - 2.52 (m, 12 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.74 - 2.84 (m, 1 H) 2.91 - 3.05 (m, 2 H) 3.18 - 3.24 (m, 3 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.32 - 3.51 (m, 2 H) 3.70 (d, J=7.93 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.10 - 4.16 (m, 1 H) 4.39 (d, J=6.99 Hz, 1 H) 4.47 (d, J=5.60 Hz, 2 H) 4.74 - 4.82 (m, 1 H) 4.89 (d, J=4.35 Hz, 1 H) 5.88 - 5.96 (m, 1 H) 6.47 (dd, J=3.34, 1.79 Hz, 1 H) 6.67 (dd, J=3.42, 0.78 Hz, 1 H) 7.15 - 7.20 (m, 1 H) 7.32 - 7.38 (m, 1 H) 7.47 (dd, J=1.87, 0.78 Hz, 1 H) 7.56 - 7.60 (m, 2 H)

[0433] 

[Table 1-5]

34		918.6	(300 MHz) : 0.79 - 0.91 (m, 6 H) 1.05 - 1.13 (m, 6 H) 1.11 - 1.27 (m, 2 H) 1.20 - 1.26 (m, 6 H) 1.29 (d, J=6.37 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.62 - 1.73 (m, 1 H) 1.78 - 1.97 (m, 1 H) 2.12 - 2.39 (m, 4 H) 2.29 - 2.30 (m, 6 H) 2.32 - 2.34 (m, 3 H) 2.39 - 2.56 (m, 4 H) 2.71 - 2.84 (m, 1 H) 2.86 - 3.09 (m, 4 H) 3.15 - 3.24 (m, 1 H) 3.23 - 3.26 (m, 3 H) 3.25 - 3.41 (m, 3 H) 3.31 - 3.32 (m, 3 H) 3.40 - 3.53 (m, 1 H) 3.70 (d, J=7.77 Hz, 1 H) 3.94 - 4.12 (m, 2 H) 4.40 (d, J=7.77 Hz, 1 H) 4.70 - 4.94 (m, 2 H) 5.93 (s, 1 H) 6.47 (dd, J=3.42, 1.71 Hz, 1 H) 6.61 - 6.67 (m, 1 H) 7.09 (d, J=7.77 Hz, 1 H) 7.26 - 7.34 (m, 1 H) 7.43 - 7.47 (m, 1 H) 7.48 - 7.54 (m, 2 H)
35		918.6	(300 MHz) : 0.86 (d, J=6.84 Hz, 6 H) 1.10 (d, J=7.31 Hz, 3 H) 1.11 - 1.27 (m, 2 H) 1.17 (d, J=7.31 Hz, 3 H) 1.23 (d, J=6.06 Hz, 3 H) 1.23 (s, 3 H) 1.30 (d, J=6.37 Hz, 3 H) 1.33 (s, 3 H) 1.48 - 1.93 (m, 7 H) 2.14 - 2.53 (m, 9 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.78 - 2.86 (m, 1 H) 2.88 - 2.97 (m, 1 H) 2.97 - 3.06 (m, 1 H) 3.21 (dd, J=10.26, 7.31 Hz, 1 H) 3.27 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.53 (m, 2 H) 3.72 (d, J=7.93 Hz, 1 H) 4.01 - 4.15 (m, 2 H) 4.41 (d, J=7.31 Hz, 1 H) 4.86 - 4.92 (m, 1 H) 4.94 (d, J=4.51 Hz, 1 H) 6.46 (dd, J=3.34, 1.79 Hz, 1 H) 6.67 (dd, J=3.42, 0.78 Hz, 1 H) 7.32 (t, J=7.85 Hz, 1 H) 7.38 - 7.42 (m, 1 H) 7.46 (dd, J=1.79, 0.70 Hz, 1 H) 7.46 - 7.51 (m, 1 H) 7.84 (s, 1 H)
36		902.6	(300 MHz) : 0.73 - 0.86 (m, 6 H) 1.00 (d, 3 H) 1.06 (d, J=7.15 Hz, 3 H) 1.08 - 1.21 (m, 2 H) 1.23 (d, J=6.06 Hz, 3 H) 1.26 (s, 3 H) 1.28 - 1.35 (m, 6 H) 1.46 - 1.73 (m, 4 H) 1.75 - 1.91 (m, 1 H) 1.93 - 2.08 (m, 1 H) 2.10 - 2.54 (m, 5 H) 2.23 - 2.26 (m, 3 H) 2.27 - 2.30 (m, 6 H) 2.60 - 2.70 (m, 1 H) 2.78 (d, J=15.85 Hz, 1 H) 2.87 - 3.11 (m, 3 H) 3.12 - 3.40 (m, 2 H) 3.21 - 3.22 (m, 3 H) 3.30 - 3.33 (m, 3 H) 3.40 - 3.54 (m, 1 H) 3.68 (d, J=7.77 Hz, 1 H) 3.98 - 4.10 (m, 2 H) 4.01 (s, 2 H) 4.38 (d, J=7.46 Hz, 1 H) 4.50 (s, 1 H) 4.84 (d, J=4.35 Hz, 1 H) 5.67 (s, 1 H) 7.36 - 7.58 (m, 4 H) 7.77 - 7.90 (m, 2 H) 7.92 - 7.99 (m, 1 H)
37		919.5	(300 MHz) : 0.80 - 0.91 (m, 6 H) 1.04 - 1.17 (m, 6 H) 1.10 - 1.20 (m, 2 H) 1.23 (d, J=5.91 Hz, 3 H) 1.25 (s, 3 H) 1.30 (d, J=6.22 Hz, 3 H) 1.32 (s, 3 H) 1.45 - 1.97 (m, 5 H) 2.02 - 2.56 (m, 6 H) 2.28 - 2.30 (m, 6 H) 2.32 - 2.35 (m, 3 H) 2.61 - 3.09 (m, 5 H) 3.15 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.53 (m, 2 H) 3.56 (s, 2 H) 3.71 (d, J=8.08 Hz, 1 H) 3.96 - 4.11 (m, 2 H) 4.41 (d, J=7.46 Hz, 1 H) 4.73 - 4.94 (m, 2 H) 6.08 (s, 1 H) 6.50 (dd, J=3.57, 2.02 Hz, 1 H) 6.78 (d, J=3.57 Hz, 1 H) 7.49 - 7.54 (m, 1 H) 7.89 - 7.95 (m, 1 H) 8.40 (d, J=2.18 Hz, 1 H) 8.84 (d, J=2.02 Hz, 1 H)
38		918.7	(500 MHz) : 0.84 (d, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.16 (d, J=7.40 Hz, 3 H) 1.15 - 1.76 (m, 8 H) 1.21 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 1.77 - 1.93 (m, 2 H) 2.14 - 2.58 (m, 14 H) 2.73 - 2.86 (m, 1 H) 2.86 - 2.97 (m, 1 H) 3.00 (t, J=9.74 Hz, 1 H) 3.17 - 3.27 (m, 1 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.60 (m, 4 H) 3.71 (d, J=7.68 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.40 (d, J=7.13 Hz, 1 H) 4.77 - 4.88 (m, 1 H) 4.91 (d, J=4.66 Hz, 1 H) 6.25 - 6.44 (m, 1 H) 6.49 (dd, J=3.29, 1.92 Hz, 1 H) 6.71 - 6.77 (m, 1 H) 7.44 (t, J=7.68 Hz, 1 H) 7.47 - 7.49 (m, 1 H) 7.60 - 7.67 (m, 1 H) 7.76 - 7.80 (m, 1 H) 8.03 - 8.09 (m, 1 H)
39		761.5	(300 MHz) : 0.78 - 0.89 (m, 6 H) 1.10 (d, J=7.31 Hz, 3 H) 1.16 (d, J=7.62 Hz, 3 H) 1.18 - 1.27 (m, 2 H) 1.20 - 1.27 (m, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.47 - 1.65 (m, 2 H) 1.77 - 1.93 (m, 1 H) 2.18 - 2.58 (m, 6 H) 2.30 (s, 6 H) 2.34 (s, 3 H) 2.73 - 2.95 (m, 2 H) 2.96 - 3.08 (m, 1 H) 3.17 - 3.24 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.36 - 3.66 (m, 4 H) 3.71 (d, J=7.93 Hz, 1 H) 3.95 - 4.01 (m, 2 H) 4.01 - 4.10 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.40 (d, J=7.46 Hz, 1 H) 4.86 - 4.98 (m, 2 H) 5.10 - 5.34 (m, 2 H) 5.77 - 5.97 (m, 1 H)
40		759.5	(300 MHz) : 0.78 - 0.89 (m, 6 H) 1.10 (d, J=7.31 Hz, 3 H) 1.17 (d, J=7.46 Hz, 3 H) 1.14 - 1.26 (m, J=7.46 Hz, 2 H) 1.20 - 1.26 (m, 6 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.48 - 1.62 (m, 2 H) 1.79 - 1.95 (m, 1 H) 2.30 (s, 3 H) 2.30 (s, 6 H) 2.33 - 2.40 (m, 1 H) 2.36 (s, 3 H) 2.41 - 2.55 (m, 2 H) 2.43 (t, J=2.41 Hz, 1 H) 2.76 - 2.85 (m, 1 H) 2.90 (d, J=14.14 Hz, 1 H) 3.02 (t, J=9.71 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.52 (m, 2 H) 3.55 - 3.64 (m, 1 H) 3.67 - 3.79 (m, 2 H) 4.01 - 4.16 (m, 2 H) 4.16 (dd, J=2.33, 1.71 Hz, 2 H) 4.41 (d, J=7.15 Hz, 1 H) 4.88 - 5.01 (m, 2 H)
41			(300 MHz) : 0.77 - 0.90 (m, 6 H) 1.01 - 1.27 (m, 2 H) 1.03 - 1.17 (m, 6 H) 1.19 - 1.27 (m, 6 H) 1.29 (d, J=6.06 Hz, 3 H) 1.33 (s, 3 H) 1.44 - 1.75 (m, 2 H) 1.78 - 1.93 (m, 1 H) 2.15 - 2.58 (m, 6 H) 2.30 - 2.32 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.71 - 3.10 (m, 3 H) 3.16 - 3.34 (m, 1 H) 3.23 - 3.25 (m, 3 H) 3.30 - 3.32 (m, 3 H) 3.36 - 3.58 (m, 4 H) 3.71 (d, J=8.24 Hz, 1 H) 3.78 - 4.19 (m, 4 H) 4.39 (d, J=7.46 Hz, 1 H) 4.81 - 5.06 (m, 3 H) 6.09 (d, J=5.28 Hz, 1 H) 6.41 - 6.50 (m, 1 H) 6.64 (d, J=3.42 Hz, 1 H) 7.04 - 7.15 (m, 1 H) 7.17 - 7.34 (m, 2 H) 7.40 - 7.55 (m, 2 H)

[0434] 

[Table 1-6]

42		901.6	(300 MHz) : 0.78 - 0.90 (m, 6 H) 1.08 (d, J=7.15 Hz, 3 H) 1.09 - 1.22 (m, 2 H) 1.17 (d, J=7.46 Hz, 3 H) 1.21 - 1.26 (m, 3 H) 1.23 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.46 - 1.70 (m, 2 H) 1.79 - 1.96 (m, 1 H) 2.18 - 2.58 (m, 6 H) 2.30 (s, 6 H) 2.38 (s, 3 H) 2.76 - 3.07 (m, 3 H) 3.17 - 3.24 (m, 1 H) 3.25 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.54 (m, 2 H) 3.60 - 3.89 (m, 3 H) 4.05 (dd, J=9.48, 6.37 Hz, 1 H) 4.09 - 4.19 (m, 1 H) 4.33 - 4.47 (m, 3 H) 4.92 (d, J=4.20 Hz, 1 H) 4.99 (s, 1 H) 6.48 (dd, J=3.42, 1.71 Hz, 1 H) 6.69 (dd, J=3.42, 0.78 Hz, 1 H) 7.30 - 7.35 (m, 2 H) 7.45 - 7.49 (m, 1 H) 7.59 - 7.66 (m, 1 H) 7.73 - 7.77 (m, 1 H)
43		905.6	(300 MHz) : 0.79 - 0.90 (m, 6 H) 1.02 - 1.37 (m, 2 H) 1.06 - 1.13 (m, 3 H) 1.16 (d, J=7.46 Hz, 3 H) 1.20 - 1.26 (m, 3 H) 1.23 - 1.24 (m, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.54 (dd, J=15.62, 5.05 Hz, 1 H) 1.67 (d, J=13.21 Hz, 1 H) 1.78 - 1.95 (m, 3 H) 2.16 - 2.41 (m, 5 H) 2.29 - 2.31 (m, 6 H) 2.34 - 2.36 (m, 3 H) 2.42 - 2.55 (m, 2 H) 2.64 - 2.75 (m, 2 H) 2.76 - 2.86 (m, 1 H) 2.91 (d, J=15.39 Hz, 1 H) 2.96 - 3.07 (m, 1 H) 3.16 - 3.24 (m, 1 H) 3.23 - 3.26 (m, 3 H) 3.32 (s, 3 H) 3.37 - 3.58 (m, 6 H) 3.71 (d, J=7.93 Hz, 1 H) 3.99 - 4.21 (m, 2 H) 4.40 (d, J=7.15 Hz, 1 H) 4.89 - 5.00 (m, 2 H) 6.44 - 6.49 (m, 1 H) 6.61 - 6.67 (m, 1 H) 7.03 - 7.11 (m, 1 H) 7.14 - 7.18 (m, 1 H) 7.19 - 7.34 (m, 1 H) 7.45 - 7.53 (m, 2 H)
44		946.8	(500 MHz) : 0.78 - 0.86 (m, 6 H) 1.04 - 1.88 (m, 16 H) 1.08 (d, J=7.13 Hz, 3 H) 1.14 (d, J=7.40 Hz, 3 H) 1.23 (d, J=9.87 Hz, 3 H) 1.27 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 2.05 - 2.60 (m, 15 H) 2.75 - 2.82 (m, 1 H) 2.88 - 3.01 (m, 2 H) 3.17 - 3.52 (m, 5 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.69 (d, J=7.68 Hz, 1 H) 4.00 - 4.07 (m, 1 H) 4.09 - 4.14 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.76 (d, 1 H) 4.89 (d, J=4.39 Hz, 1 H) 6.24 - 6.32 (m, 1 H) 6.48 (dd, J=3.43, 1.78 Hz, 1 H) 6.73 (d, J=3.57 Hz, 1 H) 7.43 (t, J=7.82 Hz, 1 H) 7.48 (d, J=1.10 Hz, 1 H) 7.63 (d, J=7.95 Hz, 1 H) 7.77 (ddd, J=7.95, 1.37, 1.10 Hz, 1 H) 8.05 (t, J=1.51 Hz, 1 H)
45		890.7	(600 MHz) : 0.82 - 0.94 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.12 (d, J=7.34 Hz, 3 H) 1.14 - 1.27 (m, 2 H) 1.20 - 1.23 (m, 3 H) 1.22 - 1.22 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.33 (s, 3 H) 1.52 (dd, J=15.36, 4.81 Hz, 1 H) 1.57 - 1.83 (m, J=11.92 Hz, 3 H) 1.90 (s, 1 H) 2.18 - 2.31 (m, 3 H) 2.28 - 2.30 (m, 6 H) 2.33 (d, J=15.13 Hz, 1 H) 2.41 (s, 3 H) 2.43 - 2.51 (m, 1 H) 2.57 (s, 1 H) 2.79 - 2.89 (m, 1 H) 3.00 (s, 1 H) 3.04 - 3.14 (m, 1 H) 3.20 (dd, J=10.32, 7.11 Hz, 1 H) 3.26 (s, 3 H) 3.30 (s, 3 H) 3.42 - 3.51 (m, 1 H) 3.55 - 3.62 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.98 - 4.16 (m, 2 H) 4.40 (d, J=6.88 Hz, 1 H) 4.88 (d, J=4.59 Hz, 1 H) 5.04 (s, 1 H) 6.45 - 6.52 (m, 1 H) 6.75 (d, J=3.21 Hz, 1 H) 7.00 (s, 1 H) 7.43 (t, J=7.79 Hz, 1 H) 7.46 - 7.49 (m, 1 H) 7.62 (d, J=7.79 Hz, 1 H) 7.78 (d, J=9.17 Hz, 1 H) 8.06 (s, 1 H)
46		904.7	(600 MHz) : 0.79 - 0.90 (m, 6 H) 1.10 (d, J=7.79 Hz, 3 H) 1.12 - 1.25 (m, 2 H) 1.17-1.26 (m, J=7.34 Hz, 9 H) 1.29 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.57 - 1.78 (m, 2 H) 1.81 - 1.96 (m, 2 H) 2.14 - 2.42 (m, 4 H) 2.28 - 2.32 (m, 6 H) 2.37 - 2.38 (m, 3 H) 2.43 - 2.57 (m, 2 H) 2.79 - 2.89 (m, 1 H) 2.89 - 2.96 (m, 1 H) 2.97 - 3.04 (m, 1 H) 3.07 - 3.30 (m, 3 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.42 - 3.52 (m, 2 H) 3.72 (d, J=7.79 Hz, 1 H) 3.72 - 3.80 (m, 1 H) 4.00 - 4.08 (m, 1 H) 4.11 (s, 1 H) 4.41 (d, J=7.34 Hz, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 4.99 (s, 1 H) 6.45 - 6.50 (m, 1 H) 6.76 (d, J=3.21 Hz, 1 H) 7.44 (t, J=7.79 Hz, 1 H) 7.46 - 7.50 (m, 1 H) 7.67 (d, J=7.34 Hz, 1 H) 7.78 (d, J=7.79 Hz, 1 H) 8.12 (s, 1 H)
47		929.7	(600 MHz) : 0.78 - 0.87 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 - 1.24 (m, 3 H) 1.22 - 1.23 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.13, 5.04 Hz, 1 H) 1.56 - 1.74 (m, 3 H) 1.77 - 1.92 (m, 3 H) 2.13 - 2.32 (m, 3 H) 2.28 - 2.31 (m, 6 H) 2.34 (d, J=15.13 Hz, 1 H) 2.37 (s, 3 H) 2.40 - 2.54 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.87 - 3.03 (m, 2 H) 3.18 - 3.22 (m, 1 H) 3.23 - 3.25 (m, 3 H) 3.31 (s, 3 H) 3.34 - 3.58 (m, 4 H) 3.70 (d, J=7.79 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.12 (s, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.80 (s, 1 H) 4.91 (d, J=5.04 Hz, 1 H) 6.49 (s, 1 H) 7.25 - 7.29 (m, 1 H) 7.54 (t, J=7.79 Hz, 1 H) 7.75 - 7.83 (m, 2 H) 7.86 (d, J=7.79 Hz, 1 H) 8.11 (d, J=7.80 Hz, 1 H) 8.38 (s, 1 H) 8.68 - 8.72 (m, 1 H)
48			(600 MHz) : 0.77 - 0.86 (m, 6 H) 1.06 (d, J=7.34 Hz, 3 H) 1.13 (d, J=7.34 Hz, 3 H) 1.15 - 1.25 (m, 2 H) 1.20 (d, J=6.42 Hz, 3 H) 1.21 (s, 3 H) 1.26 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.51 (dd, J=15.36, 4.81 Hz, 1 H) 1.53 - 1.73 (m, 3 H) 1.73 - 1.92 (m, 3 H) 2.09 - 2.60 (m, 6 H) 2.30 - 2.32 (m, 6 H) 2.33 - 2.35 (m, 3 H) 2.73 - 2.83 (m, 1 H) 2.84 - 3.03 (m, 2 H) 3.15 - 3.21 (m, 1 H) 3.21 - 3.23 (m, 3 H) 3.28 - 3.30 (m, 3 H) 3.33 - 3.60 (m, 4 H) 3.69 (d, J=7.79 Hz, 1 H) 3.96 - 4.13 (m, 2 H) 4.38 (d, J=7.34 Hz, 1 H) 4.68 - 4.91 (m, 2 H) 7.34 - 7.40 (m, 1 H) 7.52 (t, J=7.79 Hz, 1 H) 7.69 (d, J=7.79 Hz, 1 H) 7.77 (s, 1 H) 7.92 (s, 1 H) 8.01 (s, 1 H) 8.59 (d, J=5.04 Hz, 1 H) 8.82 - 8.88 (m, 1 H)

[0435] 

[Table 1-7]

49		979.8	(600 MHz) : 0.76 - 0.90 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.15 - 1.25 (m, 2 H) 1.21 - 1.23 (m, 3 H) 1.22 - 1.22 (m, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.45 - 1.96 (m, 7 H) 2.10 - 2.66 (m, 6 H) 2.29 - 2.31 (m, 6 H) 2.32 - 2.34 (m, 3 H) 2.75 - 2.84 (m, 1 H) 2.86 - 3.04 (m, 2 H) 3.17 - 3.28 (m, 1 H) 3.23 - 3.24 (m, 3 H) 3.30 (s, 3 H) 3.33 - 3.62 (m, 4 H) 3.70 (d, J=7.79 Hz, 1 H) 3.96 - 4.19 (m, 2 H) 4.39 (d; J=7.79 Hz, 1 H) 4.80 - 4.96 (m, 2 H) 7.55 - 7.62 (m, 2 H) 7.74 (t, J=7.79 Hz, 1 H) 7.77 - 7.89 (m, 1 H) 7.84 (d, J=8.25 Hz, 1 H) 7.91 (d, J=7.79 Hz, 1 H) 8.14 (d, J=8.71 Hz, 1 H) 8.19 (s, 1 H) 8.38 (s, 1 H) 9.20 (s, 1 H)
50		933.8	(600 MHz) : 0.80 - 0.93 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.16 - 1.26 (m, 2 H) 1.20 - 1.24 (m, 3 H) 1.21 - 1.23 (m, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.33 (s, 3 H) 1.46 - 1.60 (m, 3 H) 1.64 (d, J=12.38 Hz, 1 H) 1.75 (s, 2 H) 1.93 (s, 1 H) 2.11 - 2.39 (m, 4 H) 2.26 - 2.28 (m, 6 H) 2.33 - 2.36 (m, 3 H) 2.39 - 2.59 (m, 2 H) 2.74 - 2.83 (m, 1 H) 2.91 (s, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.19 (dd, J=10.09, 7.34 Hz, 1 H) 3.22 - 3.40 (m, 2 H) 3.23 - 3.25 (m, 3 H) 3.29 - 3.32 (m, 3 H) 3.41 - 3.52 (m, 2 H) 3.71 (d, J=7.79 Hz, 1 H) 3.96 - 4.09 (m, 2 H) 4.40 (d, J=6.88 Hz, 1 H) 4.69 - 5.01 (m, 2 H) 6.41 - 6.46 (m, 1 H) 6.62 (d, J=3.21 Hz, 1 H) 7.23 - 7.29 (m, 2 H) 7.29 - 7.34 (m, 1 H) 7.42 (s, 1 H) 7.68 (s, 1 H)
51			(600 MHz) : 0.81 (d, J=6.88 Hz, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.35 - 1.42 (m, 1 H) 1.45 - 1.60 (m, 3 H) 1.61 - 1.65 (m, 1 H) 1.73 - 1.79 (m, 1 H) 1.80 - 1.86 (m, 1 H) 2.10 - 2.17 (m, 1 H) 2.22 - 2.43 (m, 4 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.43 - 2.49 (m, 1 H) 2.68 (t, J=6.88 Hz, 2 H) 2.76 - 2.81 (m, 1 H) 2.91 (d, J=14.21 Hz, 1 H) 2.99 (d, J=9.63 Hz, 1 H) 3.19 (dd, J=10.09, 7.34 Hz, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.37 - 3.41 (m, 1 H) 3.42 - 3.48 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 4.02 - 4.07 (m, 1 H) 4.12 - 4.16 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.69 - 4.74 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H)
52		739.6	(600 MHz) : 0.79 - 0.89 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.12 - 1.27 (m, 2 H) 1.18 (d, J=7.34 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.66 (d, J=11.00 Hz, 1 H) 1.79 - 1.89 (m, 1 H) 2.21 - 2.42 (m, 5 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.43 - 2.52 (m, 2 H) 2.77 - 2.88 (m, 1 H) 2.96 (d, J=14.67 Hz, 1 H) 3.00 (d, J=7.34 Hz, 1 H) 3.17 - 3.23 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.38 - 3.50 (m, 2 H) 3.59 - 3.73 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.08 - 4.16 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.85 - 4.95 (m, 1 H) 4.90 (d, J=5.04 Hz, 1 H)
53		934.7	(600 MHz) : 0.78 - 0.88 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.09 - 1.26 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.21 - 1.23 (m, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.36, 4.81 Hz, 1 H) 1.55 - 1.72 (m, 3 H) 1.75 - 1.91 (m, 3 H) 2.12 - 2.32 (m, 4 H) 2.27 - 2.29 (m, 6 H) 2.34 (d, J=15.59 Hz, 1 H) 2.36 (s, 3 H) 2.42 - 2.51 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.93 (d, J=14.67 Hz, 1 H) 3.00 (t, J=8.25 Hz, 1 H) 3.20 (dd, J=10.32, 7.11 Hz, 1 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.41 (m, 1 H) 3.41 - 3.50 (m, 2 H) 3.50 - 3.60 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.11 (s, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.81 (s, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 6.39 (s, 1 H) 7.09 (dd, J=5.04, 3.67 Hz, 1 H) 7.30 (d, J=5.04 Hz, 1 H) 7.38 (d, J=3.67 Hz, 1 H) 7.42 (t, J=7.79 Hz, 1 H) 7.63 (d, J=7.79 Hz, 1 H) 7.71 (d, J=8.71 Hz, 1 H) 7.98 - 8.06 (m, 1 H)
54		934.7	(600 MHz) : 0.77 - 0.90 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.12 - 1.26 (m, 2 H) 1.17 (d, J=7.34 Hz, 3 H) 1.20 - 1.24 (m, 3 H) 1.22 - 1.23 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.13, 4.59 Hz, 1 H) 1.55 - 1.74 (m, 3 H) 1.76 - 1.91 (m, 3 H) 2.08 - 2.58 (m, 7 H) 2.29 - 2.32 (m, 6 H) 2.37 - 2.40 (m, 3 H) 2.76 - 2.86 (m, 1 H) 2.88 - 3.05 (m, 2 H) 3.17 - 3.34 (m, 2 H) 3.22 - 3.25 (m, 3 H) 3.31 - 3.32 (m, 3 H) 3.34 - 3.52 (m, 3 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.13 (s, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.77 (s, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 5.14 (s, 1 H) 6.43 - 6.47 (m, 1 H) 6.64 (d, J=3.21 Hz, 1 H) 7.01 (d, J=8.25 Hz, 1 H) 7.34 (t, J=8.02 Hz, 1 H) 7.43 (d, J=14.67 Hz, 2 H) 7.49 (d, J=7.79 Hz, 1 H)

[0436] 

[Table 1-8]

55		903.7	(600 MHz) : 0.76 - 0.86 (m, 6 H) 1.03 - 1.25 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.17 (d, J=7.34 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.21 - 1.22 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.13, 5.04 Hz, 1 H) 1.59 - 1.96 (m, 6 H) 2.10 - 2.32 (m, 4 H) 2.26 - 2.29 (m, 6 H) 2.35 (d, J=15.59 Hz, 1 H) 2.37 (s, 3 H) 2.40 - 2.50 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.93 (d, J=14.67 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.20 (dd, J=10.32, 7.11 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.49 (m, 2 H) 3.49 - 3.60 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.15 (s, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.79 (s, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 7.58 - 7.64 (m, 1 H) 7.74 - 7.78 (m, 1 H) 7.87 (d, J=8.25 Hz, 1 H) 8.11 (d, J=8.71 Hz, 1 H) 8.25 - 8.36 (m, 2 H)
56		903.7	(600 MHz) : 0.78 - 0.90 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.08 - 1.25 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 - 1.23 (m, 3 H) 1.21 - 1.23 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.13, 5.04 Hz, 1 H) 1.61 - 1.66 (m, 1 H) 1.66 - 1.94 (m, 5 H) 2.15 - 2.31 (m, 4 H) 2.26 - 2.28 (m, 6 H) 2.34 (d, J=15.13 Hz, 1 H) 2.36 (s, 3 H) 2.41 - 2.53 (m, 2 H) 2.75 - 2.86 (m, 1 H) 2.93 (d, J=14.21 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.20 (dd, J=10.32, 7.11 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.57 (m, 3 H) 3.58 - 3.68 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.12 (s, 1 H) 4.40 (d, J=7.34 Hz, 1 H) 4.84 (s, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 6.69 (s, 1 H) 7.60 (t, J=6.88 Hz, 1 H) 7.79 (t, J=6.88 Hz, 1 H) 7.92 (d, J=7.79 Hz, 1 H) 8.14 (d, J=8.71 Hz, 1 H) 8.62 (s, 1 H) 9.28 (s, 1 H)
57		903.7	(600 MHz) : 0.75 - 0.86 (m, 6 H) 1.05 (d, J=7.34 Hz, 3 H) 1.06 - 1.23 (m, 2 H) 1.10 (d, J=7.79 Hz, 3 H) 1.19 (d, J=5.96 Hz, 3 H) 1.19 (s, 3 H) 1.25 (d, J=5.96 Hz, 3 H) 1.29 (s, 3 H) 1.49 (dd, J=15.36, 4.81 Hz, 1 H) 1.54 - 1.91 (m, 6 H) 2.11 - 2.28 (m, 4 H) 2.24 - 2.26 (m, 6 H) 2.30 (d, J=15.13 Hz, 1 H) 2.35 (s, 3 H) 2.38 - 2.49 (m, 2 H) 2.72 - 2.80 (m, 1 H) 2.92 (d, J=14.21 Hz, 1 H) 2.97 (t, J=9.17 Hz, 1 H) 3.17 (dd, J=10.09, 7.34 Hz, 1 H) 3.19 (s, 3 H) 3.28 (s, 3 H) 3.31 - 3.39 (m, 1 H) 3.40 - 3.47 (m, 1 H) 3.47 - 3.63 (m, 2 H) 3.66 (d, J=7.79 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.08 (s, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.78 (s, 1 H) 4.86 (d, J=4.58 Hz, 1 H) 6.29 (s, 1 H) 7.40 (d, J=4.58 Hz, 1 H) 7.55 - 7.60 (m, 1 H) 7.70 - 7.75 (m, 1 H) 8.10 (d, J=8.71 Hz, 1 H) 8.18 (d, J=7.79 Hz, 1 H) 8.90 (d, J=4.13 Hz, 1 H)
58		839.5	(600 MHz) : 0.78 - 0.84 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.17 - 1.27 (m, 2 H) 1.22 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.33 - 1.89 (m, 7 H) 1.53 (dd, J=15.13, 4.59 Hz, 1 H) 1.61 - 1.71 (m, 1 H) 1.71 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.08 - 2.19 (m, 1 H) 2.21 - 2.55 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.75 - 2.83 (m, 1 H) 2.91 (d, J=14.67 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.18 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.43 (m, 2 H) 3.43 - 3.49 (m, 1 H) 3.51 (t, J=6.65 Hz, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.02 - 4.09 (m, 1 H) 4.12 - 4.17 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.67 - 4.75 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H)
59		918.7	(600 MHz) : 0.79 - 0.88 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.21 - 1.23 (m, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.13, 4.59 Hz, 1 H) 1.55 - 1.74 (m, 3 H) 1.75 - 1.95 (m, 3 H) 2.13 - 2.39 (m, 4 H) 2.27 - 2.29 (m, 6 H) 2.35 - 2.36 (m, 3 H) 2.41 - 2.52 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.92 (d, J=14.67 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.20 (dd, J=10.09, 6.88 Hz, 1 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.50 (m, 3 H) 3.50 - 3.58 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.13 (s, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.80 (s, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 6.36 (s, 1 H) 6.49 (dd, J=3.44, 1.60 Hz, 1 H) 6.74 (d, J=2.75 Hz, 1 H) 7.50 (d, J=1.38 Hz, 1 H) 7.68 - 7.73 (m, 2 H) 7.79 (d, J=8.25 Hz, 2 H)
60		932.7	(500 MHz) : 0.74 - 0.93 (m, 6 H) 1.07 (d, J=7.40 Hz, 3 H) 1.09 (d, J=7.68 Hz, 3 H) 1.25 (dd, J=30.17, 6.03 Hz, 8 H) 1.18 - 1.25 (m, 6 H) 1.28 (d, J=6.03 Hz, 3 H) 1.30 - 1.32 (m, 3 H) 1.75 - 1.90 (m, 3 H) 2.09 - 2.40 (m, 4 H) 2.32 (s, 6 H) 2.37 (s, 3 H) 2.40 - 2.58 (m, 2 H) 2.71 - 2.82 (m, 1 H) 2.87 - 2.96 (m, 1 H) 2.96 - 3.03 (m, 1 H) 3.18 - 3.27 (m, 1 H) 3.22 (s, 3 H) 3.29 (s, 3 H) 3.33 - 3.54 (m, 4 H) 3.69 (d, J=7.95 Hz, 1 H) 3.98 - 4.07 (m, 1 H) 4.07 - 4.16 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.64 - 4.83 (m, 1 H) 4.88 (d, J=4.39 Hz, 1 H) 6.14 - 6.28 (m, 1 H) 6.48 (dd, J=3.43, 1.78 Hz, 1 H) 6.73 (d, J=3.02 Hz, 1 H) 7.43 (t, J=7.68 Hz, 1 H) 7.48 (d, J=1.10 Hz, 1 H) 7.62 (d, J=7.13 Hz, 1 H) 7.75 - 7.81 (m, 1 H) 8.01 - 8.08 (m, 1 H)

[0437] 

[Table 1-9]

61		902.7	(500 MHz) : 0.78 - 0.88 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.15 (d, J=7.40 Hz, 3 H) 1.17 - 1.35 (m, 8 H) 1.28 (d, J=6.03 Hz, 3 H) 1.32 (s, 3 H) 1.52 (dd, J=15.08, 4.94 Hz, 1 H) 1.56 - 1.77 (m, 3 H) 1.78 - 1.97 (m, 3 H) 2.12 - 2.36 (m, 10 H) 2.38 (s, 3 H) 2.41 - 2.54 (m, 2 H) 2.73 - 2.85 (m, 1 H) 2.88 - 3.05 (m, 2 H) 3.15 - 3.27 (m, 1 H) 3.23 (s, 3 H) 3.29 - 3.33 (m, 3 H) 3.34 - 3.50 (m, 2 H) 3.50 - 3.65 (m, 2 H) 3.70 (d, J=7.95 Hz, 1 H) 3.98 - 4.09 (m, 1 H) 4.08 - 4.19 (m, 1 H) 4.39 (d, J=7.40 Hz, 1 H) 4.72 - 4.86 (m, 1 H) 4.91 (d, J=4.39 Hz, 1 H) 6.03 - 6.16 (m, 1 H) 7.41 - 7.47 (m, 1 H) 7.48 - 7.56 (m, 2 H) 7.58 (dd, J=7.13, 1.10 Hz, 1 H) 7.85 (d, J=9.05 Hz, 1 H) 7.90 (d, J=8.23 Hz, 1 H) 8.28 (d, J=8.23 Hz, 1 H)
62		791.6	(500 MHz) : 0.74 - 0.87 (m, 6 H) 1.09 (d, J=7.13 Hz, 3 H) 1.16 (d, J=7.40 Hz, 3 H) 1.18 - 1.91 (m, 14 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 5.07 Hz, 1 H) 2.05 - 2.39 (m, 16 H) 2.38 - 2.54 (m, 2 H) 2.74 - 2.84 (m, 1 H) 2.88 - 2.96 (m, 1 H) 3.00 (t, J=9.74 Hz, 1 H) 3.16 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.43 - 3.51 (m, 1 H) 3.66 (s, 3 H) 3.69 (d, J=7.95 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.66 - 4.78 (m, 1 H) 4.93 (d, J=4.39 Hz, 1 H)
63		839.6	(500 MHz) : 0.77 - 0.83 (m, 6 H) 1.05 (d, J=7.40 Hz, 3 H) 1.07 (d, J=7.40 Hz, 3 H) 1.17 - 1.26 (m, 2 H) 1.22 (d, J=6.03 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.55 (m, 1 H) 1.63 - 1.74 (m, 1 H) 1.76 - 1.90 (m, 1 H) 2.16 - 2.38 (m, 13 H) 2.38 - 2.53 (m, 2 H) 2.59 (dd, J=15.91, 4.66 Hz, 1 H) 2.65 - 2.73 (m, 1 H) 2.77 - 2.91 (m, 2 H) 2.98 - 3.07 (m, 2 H) 3.15 - 3.24 (m, 1 H) 3.21 - 3.22 (m, 3 H) 3.31 (s, 3 H) 3.36 - 3.54 (m, 2 H) 3.68 (d, J=7.95 Hz, 1 H) 3.99 - 4.07 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.37 (d, J=7.13 Hz, 1 H) 4.89 (d, J=4.66 Hz, 1 H) 5.07 - 5.15 (m, 3 H) 7.27 - 7.40 (m, 5 H)
64		749.6	(500 MHz) : 0.73 - 0.96 (m, 6 H) 1.09 (d, J=7.65 Hz, 3 H) 1.15 (d, J=7.65 Hz, 3 H) 1.18 - 1.47 (m, 14 H) 1.50 - 1.77 (m, 2 H) 1.89 - 2.91 (m, 8 H) 2.35 (br. s, 6 H) 2.63 (s, 3 H) 3.01 (d, J=9.17 Hz, 1 H) 3.17 - 3.25 (m, 1 H) 3.26 - 3.82 (m, 6 H) 3.32 (s, 3 H) 3.63 (s, 3 H) 3.83 - 3.96 (m, 1 H) 3.96 - 4.07 (m, 1 H) 4.41 (d, J=6.88 Hz, 1 H) 4.85 (d, J=4.59 Hz, 1 H) 5.06 - 5.15 (m, 1 H)
65		881.7	(500 MHz) : 0.78 - 0.85 (m, 6 H) 1.09 (d, J=6.88 Hz, 3 H) 1.13 (d, J=7.65 Hz, 3 H) 1.19 - 1.91 (m, 17 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 2.05 - 2.17 (m, 1 H) 2.16 - 2.62 (m, 17 H) 2.73 - 2.82 (m, 1 H) 2.86 - 2.95 (m, 1 H) 3.00 (t, J=9.94 Hz, 1 H) 3.16 - 3.30 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.39 (s, 1 H) 3.44 - 3.51 (m, 1 H) 3.70 (d, J=7.65 Hz, 1 H) 3.99 - 4.10 (m, 1 H) 4.11 - 4.19 (m, 1 H) 4.38 (d, J=7.65 Hz, 1 H) 4.63 - 4.75 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 5.10 (s, 2 H) 7.28 - 7.40 (m, 5 H)
66		723.6	(600 MHz) : 0.77 - 0.93 (m, 6 H) 1.04 - 1.37 (m, 20 H) 1.51 - 1.58 (m, 1 H) 1.61 - 1.71 (m, 1 H) 1.81 - 1.92 (m, 1 H) 2.18 - 2.57 (m, 6 H) 2.29 (s, 6 H) 2.32 (s, 3 H) 2.79 - 2.88 (m, 1 H) 2.90 - 3.06 (m, 2 H) 3.15 - 3.52 (m, 3 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.70 (d, J=8.25 Hz, 1 H) 3.99 - 4.15 (m, 2 H) 4.35 - 4.63 (m, 3 H) 4.86 - 4.94 (m, 1 H) 4.94 - 5.04 (m, 1 H)
67		717.5	(600 MHz) : 0.75 - 0.92 (m, 6 H) 1.05 - 1.38 (m, 20 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.55 - 1.72 (m, 1 H) 1.81 - 1.94 (m, 1 H) 2.16 - 2.54 (m, J=34.85 Hz, 6 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.77 - 3.05 (m, 3 H) 3.16 - 3.55 (m, 3 H) 3.25 (s, 3 H) 3.32 (s, 3 H) 3.72 (d, J=7.79 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.10 - 4.21 (m, 1 H) 4.41 (d, J=7.34 Hz, 1 H) 4.87 - 4.93 (m, 1 H) 5.09 - 5.31 (m, 3 H) 5.81 - 5.96 (m, 1 H)
68		932.7	(600 MHz) : 0.78 - 0.91 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.13 (d, J=6.88 Hz, 3 H) 1.17 - 1.26 (m, 2 H) 1.22 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 1 H) 1.56 - 1.72 (m, 1 H) 1.76 - 1.92 (m, 1 H) 2.16 - 2.39 (m, 4 H) 2.29 - 2.32 (m, 6 H) 2.33 - 2.35 (m, 3 H) 2.40 - 2.54 (m, 2 H) 2.74 - 2.84 (m, 1 H) 2.93 (d, J=15.13 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.17 - 3.25 (m, 1 H) 3.22 - 3.24 (m, 3 H) 3.32 (s, 3 H) 3.35 - 3.51 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.07 - 4.13 (m, 1 H) 4.18 - 4.37 (m, 4 H) 4.39 (d, J=7.34 Hz, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 4.94 - 5.06 (m, 2 H) 7.15 - 7.22 (m, 2 H) 7.37 - 7.45 (m, 2 H)
69		932.7	(600 MHz) : 0.78 - 0.90 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.27 (m, 2 H) 1.12 (d, J=7.34 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.57 - 1.71 (m, 1 H) 1.80 - 1.92 (m, 1 H) 2.12 - 2.39 (m, 13 H) 2.40 - 2.58 (m, 2 H) 2.73 - 2.83 (m, 1 H) 2.91 - 3.04 (m, 2 H) 3.17 - 3.26 (m, 1 H) 3.22 - 3.24 (m, 3 H) 3.32 (s, 3 H) 3.33 - 3.43 (m, 2 H) 3.44 - 3.54 (m, 2 H) 3.70 (d, J=7.34 Hz, 1 H) 4.00 - 4.12 (m, 2 H) 4.40 (d, J=6.88 Hz, 1 H) 4.84 (s, 1 H) 4.88 (d, J=4.58 Hz, 1 H) 5.04 (s, 2 H) 5.07 (s, 1 H) 7.17 - 7.29 (m, 2 H) 7.42 (d, J=7.34 Hz, 1 H) 7.48 (s, 1 H)

[0438] 

[Table 1-10]

70		804.7	(600 MHz) : 0.79 - 0.89 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.16 (d, J=7.79 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.36, 4.81 Hz, 1 H) 1.63 - 1.74 (m, 1 H) 1.80 - 1.93 (m, 1 H) 2.17 - 2.40 (m, 4 H) 2.28 - 2.32 (m, 6 H) 2.34 - 2.36 (m, 3 H) 2.41 - 2.55 (m, 2 H) 2.75 - 2.85 (m, 1 H) 2.93 - 3.05 (m, 2 H) 3.15 - 3.29 (m, 1 H) 3.22 - 3.24 (m, 3 H) 3.31 - 3.55 (m, 4 H) 3.31 - 3.33 (m, 3 H) 3.70 (d, J=7.79 Hz, 1 H) 3.99 - 4.15 (m, 2 H) 4.40 (d, J=6.88 Hz, 1 H) 4.54 (d, J=5.50 Hz, 2 H) 4.83 (s, 1 H) 4.89 (d, J=4.58 Hz, 1 H) 5.04 (s, 1 H) 5.19 (d, J=11.00 Hz, 1 H) 5.28 (d, J=16.97 Hz, 1 H) 5.84 - 5.96 (m, 1 H)
71		853.8	(600 MHz) : 0.77 - 0.84 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 (d, J=7.34 Hz, 3 H) 1.14 - 1.26 (m, 2 H) 121 (d, J=6.42 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.37 - 1.88 (m, 8 H) 1.53 (dd, J=15.13, 5.04 Hz, 1 H) 2.06 - 2.17 (m, 1 H) 2.19 - 2.38 (m, 4 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.39 - 2.52 (m, 2 H) 2.74 - 2.82 (m, 1 H) 2.90 (d, J=15.59 Hz, 1 H) 3.00 (t, J=8.94 Hz, 1 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.50 (m, 2 H) 3.44 (t, J=6.42 Hz, 2 H) 3.69 (d, J=7.79 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.12 - 4.18 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.47 (s, 2 H) 4.66 - 4.74 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 7.25 - 7.27 (m, 1 H) 7.29 - 7.36 (m, 4 H)
72		839.7	(600 MHz) : 0.81 (d, J=6.88 Hz, 6 H) 1.08 (d, J=6.88 Hz, 3 H) 1.09 - 1.27 (m, 2 H) 1.14 (d, J=7.34 Hz, 3 H) 1.21 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.72 (m, 5 H) 1.78 - 1.86 (m, 2 H) 2.11 - 2.17 (m, 1 H) 2.18 - 2.51 (m, 6 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.75 - 2.81 (m, 1 H) 2.90 - 2.96 (m, 1 H) 3.00 (t, J=10.09 Hz, 1 H) 3.22 (s, 3 H) 3.21 - 3.25 (m, 1 H) 3.32 (s, 3 H) 3.37 - 3.41 (m, 1 H) 3.41 - 3.51 (m, 3 H) 3.70 (d, J=7.79 Hz, 1 H) 4.02 - 4.07 (m, 1 H) 4.13 - 4.18 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.48 (s, 2 H) 4.69 - 4.75 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 7.26 - 7.36 (m, 5 H)
73		749.7	(600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 1.05 - 1.35 (m, 2 H) 1.08 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.47 - 1.87 (m, 7 H) 2.11 - 2.19 (m, 1 H) 220 - 2.39 (m, 4 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.49 (m, 2 H) 2.76 - 2.81 (m, 1 H) 2.92 (d, J=14.67 Hz, 1 H) 3.00 (t, J=9.17 Hz, 1 H) 3.18 - 3.21 (m, 1 H) 3.21 - 3.24 (m, 3 H) 3.31 (s, 3 H) 3.36 - 3.49 (m, 2 H) 3.62 - 3.67 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.11 - 4.16 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.72 - 4.77 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H)
74		954.7	(600 MHz) : 0.78 - 0.84 (m, 6 H) 1.07 (d, J=6.88 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.20 - 1.32 (m, 5 H) 1.22 (d, J=6.42 Hz, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.41 - 1.88 (m, 7 H) 2.00 - 2.13 (m, 1 H) 2.16 - 2.47 (m, 15 H) 2.71 - 2.78 (m, 1 H) 2.84 - 2.93 (m, 1 H) 2.98 - 3.03 (m, 2 H) 3.18 - 3.27 (m, 2 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.32 - 3.39 (m, 1 H) 3.44 - 3.50 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 4.00 - 4.14 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.64 - 4.68 (m, 1 H) 4.89 (d, J=5.04 Hz, 1 H) 6.50 (dd, J=3.21, 1.83 Hz, 1 H) 6.77 (d, J=3.21 Hz, 1 H) 7.50 - 7.51 (m, 1 H) 7.51 - 7.54 (m, 1 H) 7.72 (d, J=8.71 Hz, 1 H) 7.84 (d, J=7.34 Hz, 1 H) 8.13 (s, 1 H)
75		919.7	(600 MHz) : 0.74 - 0.84 (m, 6 H) 1.05 (d, J=7.34 Hz, 3 H) 1.07 - 1.23 (m, 2 H) 1.13 (d, J=7.79 Hz, 3 H) 1.17 - 1.20 (m, 3 H) 1.18 - 1.19 (m, 3 H) 1.25 (d, J=5.96 Hz, 3 H) 1.28 (s, 3 H) 1.49 (dd, J=15.13, 5.04 Hz, 1 H) 1.53 - 1.73 (m, 3 H) 1.74 - 1.98 (m, 3 H) 2.07 - 2.36 (m, 4 H) 2.23 - 2.26 (m, 6 H) 2.32 - 2.34 (m, 3 H) 2.37 - 2.47 (m, 2 H) 2.72 - 2.81 (m, 1 H) 2.90 (d, J=15.13 Hz, 1 H) 2.97 (t, J=9.40 Hz, 1 H) 3.17 (dd, J=10.32, 7.11 Hz. 1 H) 3.19 (s, 3 H) 3.28 (s, 3 H) 3.31 - 3.52 (m, 4 H) 3.66 (d, J=7.79 Hz, 1 H) 3.98 - 4.05 (m, 1 H) 4.11 (s, 1 H) 4.35 (d, J=7.34 Hz, 1 H) 4.74 (s, 1 H) 4.89 (d, J=5.04 Hz, 1 H) 6.52 (dd, J=321, 1.83 Hz, 1 H) 7.07 (d, J=3.21 Hz, 1 H) 7.52 (d, J=0.92 Hz, 1 H) 7.75 - 7.78 (m, 1 H) 7.82 (t, J=7.79 Hz, 1 H) 7.99 - 8.02 (m, 1 H) 8.10 (t, J=6.19 Hz, 1 H)
76		919.8	(600 MHz) : 0.79 - 0.90 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.36, 4.81 Hz, 1 H) 1.55 - 1.71 (m. 3 H) 1.72 - 1.94 (m, 3 H) 2.15 - 2.31 (m, 3 H) 2.26 - 2.29 (m, 6 H) 2.34 (d, J=15.59 Hz, 1 H) 2.36 (s, 3 H) 2.39 - 2.51 (m, 2 H) 2.75 - 2.84 (m, 1 H) 2.93 (d, J=12.84 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.20 (dd, J=10.09, 7.34 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.52 (m, 3 H) 3.53 - 3.63 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.00 - 4.07 (m, 1 H) 4.09 (s, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.83 (s, 1 H) 4.90 (d, J=4.58 Hz, 1 H) 6.50 - 6.53 (m, 1 H) 6.83 (d, J=3.21 Hz, 1 H) 7.54 (d, J=1.83 Hz, 1 H) 8.30 - 8.38 (m, 1 H) 8.83 (d, J=1.83 Hz, 1 H) 9.00 (d, J=1.83 Hz, 1 H)

[0439] 

[Table 1-11]

77		924.7	(600 MHz) : 0.83 - 0.94 (m, 6 H) 1.14 (d, J=7.34 Hz, 3 H) 1.15 - 1.31 (m, 2 H) 1.21 (d, J=7.34 Hz, 3 H) 1.26 (d, J=5.96 Hz, 3 H) 1.27 (s, 3 H) 1.33 (d, J=6.42 Hz, 3 H) 1.36 (s, 3 H) 1.54 - 1.73 (m, 4 H) 1.74 - 2.10 (m, 3 H) 2.16 - 2.45 (m, 4 H) 2.31 - 2.34 (m, 6 H) 2.40 - 2.41 (m, 3 H) 2.45 - 2.58 (m, 2 H) 2.79 - 2.89 (m, 1 H) 2.96 (d, J=13.30 Hz, 1 H) 3.01 - 3.09 (m, 1 H) 3.25 (dd, J=10.09, 7.34 Hz, 1 H) 3.28 (s, 3 H) 3.36 (s, 3 H) 3.38 - 3.61 (m, 4 H) 3.75 (d, J=7.79 Hz, 1 H) 4.06 - 4.13 (m, 1 H) 4.17 (s, 1 H) 4.44 (d, J=6.88 Hz, 1 H) 4.84 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 6.39 (s, 1 H) 6.48 - 6.52 (m, 1 H) 6.62 - 6.65 (m, 1 H) 7.21 (d, J=4.13 Hz, 1 H) 7.45 - 7.52 (m, 2 H)
78		908.8	(600 MHz) : 0.77 - 0.88 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.13, 5.04 Hz, 1 H) 1.55 - 1.71 (m, 3 H) 1.72 - 1.94 (m, 3 H) 2.12 - 2.20 (m, 1 H) 2.21 - 2.35 (m, 3 H) 2.26 - 2.28 (m, 6 H) 2.34 - 2.37 (m, 3 H) 2.39 - 2.51 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.92 (d, J=15.59 Hz, 1 H) 3.00 (t, J=9.63 Hz, 1 H) 3.20 (dd, J=10.09, 7.34 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.53 (m, 4 H) 3.69 (d, J=8.25 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.12 (s, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.78 (s, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 6.44 - 6.51 (m, 2 H) 6.60 (d, J=3.21 Hz, 1 H) 6.70 (d, J=3.67 Hz, 1 H) 7.14 (d, J=3.67 Hz, 1 H) 7.43 - 7.47 (m, 1 H)
79		825.8	(600 MHz) : 0.73 - 0.80 (m, 6 H) 1.03 - 1.06 (m, 7 H) 1.19 (d, J=6.42 Hz, 3 H) 1.19-1.20 (m, 3 H) 1.21 - 1.23 (m, 1 H) 1.25 (d, J=6.42 Hz, 3 H) 1.29 (s, 3 H) 1.50 (dd, J=15.13, 5.04 Hz, 1 H) 1.62 (d, J=12.38 Hz, 1 H) 1.74 - 1.85 (m, 2 H) 1.97 - 2.17 (m, 2 H) 2.18 - 2.30 (m, 3 H) 2.26 (s, 6 H) 2.33 (s, 3 H) 2.34 - 2.49 (m, 3 H) 2.70 - 2.77 (m, 1 H) 2.92 - 3.00 (m, 2 H) 3.13 - 3.20 (m, 1 H) 3.19 (s, 3 H) 3.28 (s, 3 H) 3.34 - 3.46 (m, 3 H) 3.46 - 3.51 (m, 1 H) 3.66 (d, J=8.25 Hz, 1 H) 3.98 - 4.05 (m, 1 H) 4.10 - 4.15 (m, 1 H) 4.34 (d, J=6.88 Hz, 1 H) 4.42 (s, 2 H) 4.85 - 4.93 (m, 1 H) 4.90 (d, J=4.58 Hz, 1 H) 7.20 - 7.32 (m, 5 H)
80		788.7	(600 MHz) : 0.74 - 0.79 (m, 6 H) 1.04 (d, J=7.34 Hz, 3 H) 1.06 - 1.21 (m, 2 H) 1.11 (d, J=7.34 Hz, 3 H) 1.16 (d, J=8.42 Hz, 3 H) 1.18 (s, 3 H) 1.23 (d, J=6.42 Hz, 3 H) 1.27 (s, 3 H) 1.31 - 1.36 (m, 2 H) 1.40 - 1.52 (m, 5 H), 1.60 (d, J=12.38 Hz, 1 H) 1.64 - 1.85 (m, 2 H) 2.13 - 2.48 (m, 12 H) 2.24 (s, 6 H) 2.31 (s, 3 H) 2.69 - 2.77 (m, 1 H) 2.81 (d, J=15.13 Hz, 1 H) 2.95 (t, J=9.86 Hz, 1 H) 3.10 - 3.21 (m, 1 H) 3.17 (s, 3 H) 3.27 (s, 3 H) 3.36 - 3.46 (m, 2 H) 3.65 (d, J=7.79 Hz, 1 H) 3.96 - 4.03 (m, 1 H) 4.06 - 4.12 (m, 1 H) 4.33 (d, J=7.34 Hz, 1 H) 4.75 - 4.96 (m, 1 H) 4.88 (d, J=5.04 Hz, 1 H)
81		763.7	(600 MHz) : 0.77 - 0.85 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 - 1.26 (m, 2 H) 1.15 (d, J=7.34 Hz, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.36 - 1.91 (m, 10 H) 2.09 - 2.20 (m, 1 H) 2.20 - 2.32 (m, 3 H) 2.29 (s, 6 H) 2.33 - 2.52 (m, 3 H) 2.36 (s, 3 H) 2.76 - 2.83 (m, 1 H) 2.92 (d, J=17.42 Hz, 1 H) 3.00 (t, J=9.40 Hz, 1 H) 3.17 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.51 (m, 2 H) 3.59 - 3.65 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.68 - 4.78 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H)
82		923.8	(600 MHz) : 0.80 - 0.85 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.17 - 1.26 (m, 2 H) 1.22 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.93 (m, 3 H) 2.18 - 2.60 (m, 13 H) 2.35 (s, 6 H) 2.37 (s, 3 H) 2.72 - 2.82 (m, 1 H) 2.87 (d, J=16.51 Hz, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.16 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.39 - 3.52 (m, 6 H) 3.70 (d, J=7.79 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.07 - 4.13 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 4.94 - 4.98 (m, 1 H) 5.11 (s, 2 H) 7.27 - 7.38 (m, 5 H)
83		774.7	(600 MHz) : 0.78 - 0.87 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.11 - 1.27 (m, 8 H) 1.15 (d, J=7.79 Hz, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.13, 5.04 Hz, 1 H) 1.60 - 1.80 (m, 4 H) 1.65 (d, J=12.84 Hz, 1 H) 1.80 - 1.89 (m, 1 H) 2.21 - 2.40 (m, 5 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.42 - 2.53 (m, 6 H) 2.56 (dd, J=12.15, 7.11 Hz, 1 H) 2.66 - 2.75 (m, 1 H) 2.75 - 2.83 (m, 1 H) 2.88 (d, J=14.21 Hz, 1 H) 2.98 - 3.03 (m, 1 H) 3.17 - 3.25 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.41 - 3.51 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.12 - 4.18 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.85 - 4.91 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H)

[0440] 

[Table 1-12]

84		735.6	(600 MHz) : 0.83 (d, J=6.88 Hz, 3 H) 0.85 (d, J=4.59 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.24 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.19 (d, J=5.96 Hz, 3 H) 1.21 (s, 3 H) 1.25 (d, J=5.96 Hz, 3 H) 1.29 (s, 3 H) 1.52 (dd, J=15.38, 4.81 Hz, 1 H) 1.58 - 1.70 (m, 1 H) 1.71 - 1.81 (m. 2 H) 1.81 - 1.91 (m, 1 H) 2.15 - 2.31 1 (m, 5 H) 2.26 (s, 6 H) 2.32 - 2.54 (m, 3 H) 2.35 (s, 3 H) 2.73 - 2.82 (m, 1 H) 2.90 - 3.01 (m, 1 H) 2.98 (t, J=9.86 Hz, 1 H) 3.16 - 3.21 (m, 2 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.41 - 3.50 (m, 2 H) 3.60 - 3.67 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.98 - 4.06 (m, 1 H) 4.06 - 4.13 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.87 (d, J=4.58 Hz, 1 H) 4.93 - 5.01 (m, 1 H)
85		789.8	(600 MHz) : 0.78 - 0.86 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 1 H) 1.60 - 1.66 (m, 1 H) 1.79 - 1.90 (m, 1 H) 2.20 - 2.33 (m, 3 H) 2.27 (s, 6 H) 2.34 - 2.54 (m, 9 H) 2.35 (s, 3 H) 2.74 - 2.90 (m, 6 H) 2.99 (d, J=9.17 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.41 - 3.49 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.01 - 4.07 (m, 1 H) 4.08 - 4.14 (m, 1 H) 4.37 (d, J=7.34 Hz, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 4.93 - 4.98 (m, 1 H)
86			(600 MHz) : 0.78 - 0.85 (m, 6 H) 0.91 (t, J=7.34 Hz, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.11 - 1.27 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.33 - 1.90 (m, 6 H) 1.53 (dd, J=15.13, 5.04 Hz, 1 H) 2.10 - 2.53 (m, 6 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.68 (t, J=7.11 Hz, 2 H) 2.75 - 2.82 (m, 1 H) 2.91 (d, J=14.67 Hz, 1 H) 3.00 (d, J=9.63 Hz, 1 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.43 (m, 1 H) 3.42 - 3.51 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.67 - 4.78 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H)
87		803.8	(600 MHz) : 0.77 - 0.88 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.21 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.22 (d, J=6.42 Hz, 3 H) 1.22 - 1.23 (m, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 1 H) 1.66 - 1.73 (m, 1 H) 1.79 - 1.91 (m, 1 H) 2.15 - 2.65 (m, 16 H) 2.30 (s, 3 H) 2.33 (s, 6 H) 2.36 (s, 3 H) 2.74 - 2.81 (m, 1 H) 2.88 (d, J=14.67 Hz, 1 H) 3.00 (d, J=9.63 Hz, 1 H) 3.17 - 3.26 (m, 4 H) 3.32 (s, 3 H) 3.39 - 3.52 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 3.99 - 4.07 (m, 1 H) 4.08 - 4.14 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 4.93 - 4.99 (m, 1 H)
88		771.7	(600 MHz) : 0.82 (d, J=6.88 Hz, 3 H) 0.85 (d, J=6.42 Hz, 3 H) 0.88 - 0.99 (m, 3 H) 1.07 (d, J=7.34 Hz, 3 H) 1.09 - 1.25 (m, 8 H) 1.27 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.49 (dd, J=15.36, 4.81 Hz, 1 H) 1.65 (d, J=13.76 Hz, 1 H) 1.74 - 1.91 (m, 1 H) 2.18 - 2.36 (m, 4 H) 2.28 (s, 6 H) 2.39 (s, 3 H) 2.43 - 2.53 (m, 2 H) 2.65 - 2.74 (m, 1 H) 2.94 - 3.01 (m, 1 H) 3.06 (d, J=15.59 Hz, 1 H) 3.15 - 3.21 (m, 1 H) 3.20 (s, 3 H) 3.29 (s, 3 H) 3.35 - 3.49 (m, 2 H) 3.66 (d, J=7.79 Hz, 1 H) 3.97 - 4.05 (m, 2 H) 4.08 (dd, J=14.21, 3.21 Hz, 1 H) 4.19 - 4.29 (m, 1 H) 4.37 (d, J=6.88 Hz, 1 H) 4.82 (d, J=4.58 Hz, 1 H) 4.91 - 5.02 (m, 1 H) 6.90 (s, 1 H) 7.02 (s, 1 H) 7.46 (s, 1 H)
89		847.5	(600 MHz) : 0.75 - 0.91 (m, 9 H) 1.03 (d, J=7.34 Hz, 3 H) 1.06 - 1.28 (m, 11 H) 1.29 (s, 3 H) 1.43 (dd, J=15.13, 4.59 Hz, 1 H) 1.51 - 1.88 (m, 2 H) 2.15 - 2.34 (m, 11 H) 2.39 (s, 3 H) 2.42 - 2.54 (m, 2 H) 2.66 - 2.74 (m, 1 H) 2.94 (t, J=9.40 Hz, 1 H) 3.05 - 3.20 (m, 2 H) 3.17 (s, 3 H) 3.24 (s, 3 H) 3.25 - 3.47 (m, 2 H) 3.63 (d, J=8.25 Hz, 1 H) 3.92 - 4.03 (m, 2 H) 4.11 (dd, J=14.21, 2.75 Hz, 1 H) 4.21 - 4.29 (m, 1 H) 4.33 (d, J=7.34 Hz, 1 H) 4.77 (d, J=4.59 Hz, 1 H) 4.93 - 5.04 (m, 1 H) 7.24 (s, 1 H) 7.26 (dd, J=8.02, 4.81 Hz, 1 H) 7.51 (s, 1 H) 8.03 (td, J=7.91, 2.06, 1.95 Hz, 1 H) 8.43 (dd, J=4.81, 1.60 Hz, 1 H) 8.90 (d, J=1.83 Hz, 1 H)
90		749.6	(500 MHz) : 0.85 - 0.96 (m, 6 H) 1.11 (d, J=7.65 Hz, 3 H) 1.15 - 1.34 (m, 8 H) 1.18 (d, J=6.88 Hz, 3 H) 1.26 (d, J=6.12 Hz, 3 H) 1.30 (s, 3 H) 1.53 (dd, J=14.91, 4.97 Hz, 1 H) 1.65 - 1.73 (m, 1 H) 1.89 - 2.00 (m, 1 H) 2.15 - 2.42 (m, 13 H) 2.44 - 2.54 (m, 1 H) 2.55 - 2.63 (m, 1 H) 2.64 - 2.76 (m, 1 H) 2.90 - 2.97 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.03 - 3.13 (m, 1 H) 3.19 - 3.29 (m, 1 H) 3.26 (s, 3 H) 3.33 (s, 3 H) 3.44 - 3.56 (m, 2 H) 3.70 - 3.77 (m, 1 H) 3.73 (s, 3 H) 3.99 - 4.08 (m, 1 H) 4.08 - 4.27 (m, 1 H) 4.44 (d, J=6.88 Hz, 1 H) 4.72 - 4.78 (m, 1 H) 5.06 - 5.15 (m, 1 H)
91		790.7	(500 MHz) : 0.74 - 0.87 (m, 6 H) 1.09 (d, J=7.13 Hz, 3 H) 1.15 (d, J=7.40 Hz, 3 H) 1.18 - 1.91 (m, 17 H) 1.28 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 2.09 - 2.58 (m, 9 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.71 - 2.85 (m, 1 H) 2.86 - 2.96 (m, 1 H) 3.00 (t, J=9.60 Hz, 1 H) 3.18 - 3.25 (m, 4 H) 3.32 (s, 3 H) 3.35 - 3.43 (m, 1 H) 3.43 - 3.52 (m, 1 H) 3.66 - 3.73 (m, J=7.95 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.09 - 4.19 (m, 1 H) 4.39 (d, J=7.40 Hz, 1 H) 4.65 - 4.80 (m, 1 H) 4.92 (d, J=4.66 Hz, 1 H) 5.17 - 5.32 (m, 1 H) 5.33 - 5.53 (m, 1 H)

[0441] 

[Table 1-13]

92		869.7	(600 MHz) : 0.78 - 0.88 (m, 6 H) 1.08 (d, J=7.79 Hz, 3 H) 1.12 (d, J=7.34 Hz, 3 H) 1.17 - 1.30 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.13, 4.59 Hz, 1 H) 1.61 - 1.70 (m, 1 H) 1.79 - 1.92 (m, 1 H) 2.18 - 2.37 (m, 4 H) 2.27 - 2.30 (m, 6 H) 2.34 - 2.35 (m, 3 H) 2.42 - 2.52 (m, 2 H) 2.73 - 2.83 (m, 1 H) 2.93 - 3.04 (m, 2 H) 3.16 - 3.41 (m, 3 H) 3.22 - 3.24 (m, 3 H) 3.30 - 3.32 (m, 3 H) 3.42 - 3.58 (m, 3 H) 3.64 - 3.77 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 3.99 - 4.14 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.85 (s, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 4.94 - 5.10 (m, 3 H) 6.60 (d, J=9.17 Hz, 1 H) 6.63 (s, 1 H) 6.69 (d, J=7.34 Hz, 1 H) 7.11 (t, J=7.79 Hz, 1 H)
93		879.7	(600 MHz) : 0.77 - 0.90 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.13 (d, J=7.34 Hz, 3 H) 1.16 - 1.30 (m, 2 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 - 1.24 (m, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.58 (m, 2 H) 1.79 - 1.93 (m, 1 H) 2.07 - 2.40 (m, 14 H) 2.39 - 2.56 (m, 2 H) 2.74 - 2.83 (m, 1 H) 2.93 - 3.05 (m, 2 H) 3.17 - 3.27 (m, 1 H) 3.22 - 3.24 (m, 3 H) 3.32 (s, 3 H) 3.33 - 3.56 (m, 4 H) 3.70 (d, J=7.79 Hz, 1 H) 3.96 - 4.16 (m, 2 H) 4.40 (d, J=6.88 Hz, 1 H) 4.79 - 4.91 (m, 2 H) 5.10 (s, 2 H) 5.16 (s, 1 H) 7.45 (t, J=7.79 Hz, 1 H) 7.52 - 7.69 (m, 3 H)
94		920.8	(600 MHz) : 0.77 - 0.91 (m, 6 H) 1.02 - 1.37 (m, 20 H) 1.47 - 1.56 (m, 1 H) 1.61 - 1.72 (m, 1 H) 1.80 - 1.93 (m, 1 H) 2.17 - 2.54 (m, 6 H) 2.30 (s, 6 H) 2.35 (s, 3 H) 2.72 - 2.82 (m, 1 H) 2.93 - 3.05 (m, 2 H) 3.15 - 3.56 (m, 5 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.69 (d, J=7.79 Hz, 1 H) 3.99 - 4.13 (m, 2 H) 4.39 (d, J=7.34 Hz, 1 H) 4.78 - 4.92 (m, 2 H) 5.03 - 5.16 (m, 3 H) 6.42 - 6.51 (m, 1 H) 6.62 - 6.71 (m, 1 H) 7.19 - 7.69 (m, 5 H)
95		854.7	(600 MHz) : 0.81 - 0.89 (m, 6 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 - 1.26 (m, 2 H) 1.19 (d, J=7.34 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.55 (dd, J=15.13, 5.04 Hz, 1 H) 1.62 - 1.72 (m, 1 H) 1.77 - 1.93 (m, 3 H) 2.19 - 2.42 (m, 7 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.44 - 2.52 (m, 2 H) 2.78 - 2.87 (m, 1 H) 2.90 - 3.15 (m, 4 H) 3.17 - 3.26 (m, 1 H) 3.25 (s, 3 H) 3.32 (s, 3 H) 3.38 - 3.51 (m, 3 H) 3.71 (d, J=7.79 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.40 (d, J=7.34 Hz, 1 H) 4.86 - 4.98 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 5.34 - 5.50 (brs, 1 H) 7.11 (d, J=7.34 Hz, 1 H) 7.18 (t, J=7.34 Hz, 1 H) 7.34 (t, J=8.02 Hz, 2 H)
96		920.8	(500 MHz) : 0.75 - 0.90 (m, 6 H) 1.06 (d, J=7.13 Hz, 3 H) 1.11 (d, J=7.40 Hz, 3 H) 1.11 - 1.39 (m, 2 H) 1.20 - 1.24 (m, 6 H) 1.27 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.41 - 2.06 (m, 3 H) 2.15 - 2.55 (m, 14 H) 2.55 - 2.69 (m, 1 H) 2.72 - 2.84 (m, 1 H) 2.88 - 2.97 (m, 1 H) 3.00 (d, J=6.86 Hz, 1 H) 3.20 - 3.32 (m, 1 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.35 - 3.54 (m, 2 H) 3.69 (d, J=7.68 Hz, 1 H) 3.97 - 4.13 (m, 2 H) 4.16 - 4.47 (m, 5 H) 4.84 - 4.91 (m, 1 H) 4.93 - 5.08 (m, 2 H) 6.46 (dd, J=329, 1.92 Hz, 1 H) 6.66 (dd, J=3.43, 0.69 Hz, 1 H) 7.14 - 7.19 (m, 1 H) 7.34 (m, 1 H) 7.44 - 7.48 (m, 1 H) 7.53 - 7.61 (m, 2 H)
97		854.8	(500 MHz) : 0.74 - 0.88 (m, 6 H) 1.06 (d, J=6.88 Hz, 3 H) 1.09 - 1.75 (m, 4 H) 1.13 (d, J=7.65 Hz, 3 H) 1.21 - 1.25 (m, 6 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.81 - 1.90 (m, 1 H) 2.12 - 2.56 (m, 16 H) 2.73 - 2.85 (m, 1 H) 2.90 - 2.99 (m, 1 H) 3.01 (t, J=9.56 Hz, 1 H) 3.22 (s, 3 H) 3.25 - 3.36 (m, 1 H) 3.31 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.46 - 3.57 (m, 1 H) 3.70 (d, J=7.65 Hz, 1 H) 3.98 - 4.05 (m, 1 H) 4.05 - 4.13 (m, 1 H) 4.17 - 4.38 (m, 4 H) 4.41 (d, J=6.88 Hz, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 4.92 - 5.02 (m, 1 H) 7.26 - 7.36 (m, 5 H)
98		855.8	(600 MHz) : 0.78 - 0.89 (m, 6 H) 1.08 (d, J=7.79 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 - 1.28 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 1 H) 1.65 (d, J=13.30 Hz, 1 H) 1.80 - 1.91 (m, 1 H) 2.18 - 2.38 (m, 4 H) 2.27 - 2.29 (m, 6 H) 2.33 - 2.35 (m, 3 H) 2.40 - 2.54 (m, 2 H) 2.71 - 2.83 (m, 1 H) 2.92 - 3.05 (m, 2 H) 3.19 (dd, J=10.09, 7.34 Hz, 1 H) 3.22 (s, 3 H) 3.30 - 3.32 (m, 3 H) 3.30 - 3.54 (m, 4 H) 3.69 (d, J=8.25 Hz, 1 H) 3.97 - 4.13 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.84 (s, 1 H) 4.88 (d, J=4.59 Hz, 1 H) 5.09 (s, 2 H) 5.15 (s, 1 H) 7.26 - 7.30 (m, 1 H) 7.67 (d, J=7.79 Hz, 1 H) 8.55 (d, J=5.04 Hz, 1 H) 8.58 (s, 1 H)

[0442] 

[Table 1-14]

99		889.7	(600 MHz) : 0.77 - 0.86 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.09 - 1.26 (m, 2 H) 1.13 (d, J=7.79 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 128 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.46 - 1.69 (m, 6 H) 1.84 (s, 1 H) 2.08 - 2.20 (m, 1 H) 2.21 - 2.31 (m, 2 H) 2.27 - 229 (m, 6 H) 2.32 - 2.37 (m, 1 H) 2.35 - 2.36 (m, 3 H) 2.37 - 2.51 (m, 2 H) 2.74 (t, J=6.65 Hz, 2 H) 2.76 - 2.82 (m, 1 H) 2.92 (d, J=14.21 Hz, 1 H) 3.00 (d, J=8.71 Hz, 1 H) 320 (dd, J=10.09, 7.34 Hz, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.33 - 3.50 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.14 (s, 1 H) 4.25 (s, 2 H) 4.38 (d, J=7.34 Hz, 1 H) 4.74 (s, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 7.43 (d, J=4.13 Hz, 1 H) 7.53 - 7.59 (m, 1 H) 7.67 - 7.73 (m, 1 H) 8.07 (d, J=825 Hz, 1 H) 8.11 (d, J=7.79 Hz, 1 H) 8.86 (d, J=4.13 Hz, 1 H)
100			(600 MHz) : 0.72 - 0.85 (m, 6 H) 1.00 - 1.35 (m, 2 H) 1.06 (d, J=5.04 Hz, 3 H) 1.11 (d, J=7.79 Hz, 3 H) 1.18 - 1.25 (m, 6 H) 1.27 (d, J=6.42 Hz, 3 H) 1.29 - 1.31 (m, 3 H) 1.38 - 1.68 (m, 6 H) 1.74 - 1.86 (m, 1 H) 1.92 - 2.42 (m, 12 H) 2.21 - 222 (m, 6 H) 2.45 (t, J=6.88 Hz, 2 H) 2.71 - 2.81 (m, 1 H) 2.90 (none, 1 H) 2.85 - 2.92 (m, 1 H) 2.99 (t, J=9.63 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.19 - 3.21 (m, 3 H) 3.28 - 3.30 (m, 3 H) 3.33 - 3.41 (m, 1 H) 3.42 - 3.56 (m, 1 H) 3.68 (d, J=7.79 Hz, 1 H) 3.82 - 3.92 (m, 2 H) 3.95 - 4.07 (m, 1 H) 4.07 - 4.18 (m, 1 H) 4.38 (d, J=7.79 Hz, 1 H) 4.66 (s, 1 H) 4.90 (d, J=4.58 Hz, 1 H) 7.38 (d, J=4.13 Hz, 1 H) 7.49 - 7.55 (m, 1 H) 7.65 - 7.71 (m, 1 H) 8.09 (d, J=8.25 Hz, 1 H) 8.21 (d, J=8.71 Hz, 1 H) 8.83 (d, J=4.13 Hz, 1 H)
101		890.6	(600 MHz) : 0.78 - 0.84 (m, 6 H) 1.05 - 1.10 (m, 3 H) 1.06 - 1.29 (m, 2 H) 1.13 (d, J=7.34 Hz, 3 H) 1.21 - 1.25 (m, 6 H) 1.28 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.57 - 1.91 (m, 7 H) 2.06 - 2.17 (m, 1 H) 2.18 - 2.47 (m, 12 H) 2.34 - 2.36 (m, 3 H) 2.75 - 2.83 (m, 1 H) 2.90 - 2.97 (m, 1 H) 3.01 (t, J=10.09 Hz, 1 H) 3.16 - 3.27 (m, 1 H) 3.21 - 322 (m, 3 H) 3.31 (s, 3 H) 3.39 (s, 1 H) 3.47 (s, 1 H) 3.54 - 3.65 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.03 (s, 1 H) 4,14 (s, 1 H) 4.39 (s, 1 H) 4.74 (s, 1 H) 4.91 (s, 1 H) 4.96 (s, 2 H) 7.45 (d, J=4.58 Hz, 1 H) 7.53 - 7.59 (m, 1 H) 7.69 - 7.74 (m, 1 H) 7.98 (d, J=8.25 Hz, 1 H) 8.12 (d, J=825 Hz, 1 H) 8.89 (d, J=4.13 Hz, 1 H)
102		730.5	(500 MHz) : 0.82 - 0.93 (m, 6 H) 1.10 (d, J=7.64 Hz, 3 H) 1.12 - 1.31 (m, 2 H) 1.18 - 1.23 (m, 6 H) 1.24 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.51 - 1.71 (m, 2 H) 1.83 - 1.93 (m, 1 H) 2.18 - 2.41 (m, 4 H) 2.30 (s, 6 H) 2.37 (d, J=15.29 Hz, 1 H) 2.40 (s, 3 H) 2.44 - 2.61 (m. 2 H) 2.66 - 2.75 (m, 2 H) 2.82 - 2.87 (m, 1 H) 2.97 - 3.08 (m, 2 H) 3.16 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.29 - 3.38 (m, 1 H) 3.33 (s, 3 H) 3.43 - 3.52 (m, 1 H) 3.70 (d, J=7.64 Hz, 1 H) 3.92 - 4.10 (m, 2 H) 4.41 (d, J=7.26 Hz, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 4.94 - 5.03 (m, 1 H)
103		744.5	(500 MHz) : 0.82 - 0.93 (m, 6 H) 1.10 (d, J=7.64 Hz, 3 H) 1.12 - 1.31 (m, 2 H) 1.18 - 1.23 (m, 6 H) 124 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.51 - 1.71 (m, 2 H) 1.83 - 1.93 (m, 1 H) 2.18 - 2.41 (m, 4 H) 2.30 (s, 6 H) 2.37 (d, J=15.29 Hz, 1 H) 2.40 (s, 3 H) 2.44 - 2.61 (m, 2 H) 2.66 - 2.75 (m, 2 H) 2.82 - 2.87 (m, 1 H) 2.97 - 3.08 (m, 2 H) 3.18 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.29 - 3.38 (m, 1 H) 3.33 (s, 3 H) 3.43 - 3.52 (m, 1 H) 3.70 (d, J=7.64 Hz, 1 H) 3.92 - 4.10 (m, 2 H) 4.41 (d, J=7.26 Hz, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 4.94 - 5.03 (m, 1 H)
104		758.6	(500 MHz) : 0.75 - 0.88 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.11 - 1.27 (m, 2 H) 1.15 (d, J=7.26 Hz, 3 H) 1.22 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.29, 4.97 Hz, 1 H) 1.57 - 1.98 (m, 7 H) 2.11 - 2.20 (m, 1 H) 2.19 - 2.52 (m, 7 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.73 - 2.84 (m, 1 H) 2.94 (d, J=14.91 Hz, 1 H) 3.00 (t, J=9.75 Hz, 1 H) 3.15 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.33 - 3.42 (m, 1 H) 3.42 - 3.50 (m, 1 H) 3.69 (d, J=8.03 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.38 (d, J=7.26 Hz, 1 H) 4.69 - 4.81 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H)
105		778.5	(600 MHz) : 0.81 - 0.86 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.59 - 1.68 (m, 1 H) 1.82 - 1.88 (m, 1 H) 2.20 - 2.32 (m, 3 H) 2.24 (d, J=10.09 Hz, 1 H) 2.29 (s, 6 H) 2.35 (d, J=14.67 Hz, 1 H) 2.35 (s, 3 H) 2.43 - 2.51 (m, 2 H) 2.77 - 2.83 (m, 1 H) 2.95 - 2.99 (m, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.31 - 3.42 (m, 2 H) 3.42 - 3.54 (m, 2 H) 3.64 (s, 3 H) 3.70 (d, J=7.79 Hz, 1 H) 4.02 - 4.06 (m, 1 H) 4.07 - 4.13 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.80 - 4.84 (m, 1 H) 4.90 (d, J=4.58 Hz, 1 H) 4.96 - 5.02 (m, 1 H)

[0443] 

[Table 1-15]

106		792.5	(600 MHz) : 0.80 - 0.87 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.09 - 1.26 (m, 5 H) 1.16 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 123 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=14.90, 4.81 Hz, 1 H) 1.61 - 1.68 (m, 1 H) 1.82 - 1.89 (m, 1 H) 2.21 - 2.38 (m, 5 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.42 - 2.51 (m, 2 H) 2.78 - 2.82 (m, 1 H) 2.95 - 2.98 (m, 1 H) 3.00 (t, J=10.09 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.32 - 3.42 (m, 2 H) 3.42 - 3.51 (m, 2 H) 3.69 (d, J=7.79 Hz, 1 H) 4.01 - 4.12 (m, 4 H) 4.39 (d, J=6.88 Hz, 1 H) 4.79 - 4.84 (m, 1 H) 4.90 (d, J=4.58 Hz, 1 H) 4.92 - 4.96 (m, 1 H)
107		778.5	(600 MHz) : 0.80 - 0.86 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.22 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.52 - 1.56 (m, 1 H) 1.61 - 1.68 (m, 1 H) 1.83 - 1.87 (m, 1 H) 2.21 - 2.38 (m, 5 H) 2.29 (s, 6 H) 2.34 (s, 3 H) 2.43 - 2.50 (m, 2 H) 2.78 (d, J=4.59 Hz, 3 H) 2.79 - 2.83 (m, 1 H) 2.89 - 2.94 (m, 1 H) 3.00 (t, J=10.09 Hz, 1 H) 3.19 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.38 - 3.50 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.02 - 4.07 (m, 1 H) 4.08 - 4.13 (m, 1 H) 4.17 - 4.25 (m, 2 H) 4.39 (d, J=6.88 Hz, 1 H) 4.55 - 4.60 (m, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 4.93 - 4.97 (m, 1 H)
108		792.6	(600 MHz) : 0.79 - 0.84 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.13, 5.04 Hz, 1 H) 1.63 - 1.69 (m, 1 H) 1.80 - 1.87 (m, 1 H) 2.25 (d, J=10.55 Hz, 1 H) 2.24 - 2.38 (m, 4 H) 2.28 (s, 6 H) 2.34 (s, 3 H) 2.42 - 2.50 (m, 2 H) 2.79 - 2.84 (m, 1 H) 2.85 (s, 3 H) 2.90 (s, 3 H) 2.95 (d, J=16.05 Hz, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.41 - 3.50 (m, 2 H) 3.69 (d, J=7.79 Hz, 1 H) 4.02 - 4.07 (m, 1 H) 4.11 - 4.13 (m, 1 H) 4.15 - 4.19 (m, 1 H) 4.27 (dd, J=11.46, 4.13 Hz, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 4.95 - 5.00 (m, 1 H)

Example 7

[0444] 

(1) The compound obtained in Example 1 (10.0 g) was dissolved in tetrahydrofuran (30 ml), the solution was added with (R)-1,2-epoxybutane (3.62 g) and ytterbium triflate monohydrate (624 mg), and the mixture was stirred at 90°C for 1.25 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain a 10a-N-(2-hydroxybutyl) compound (4.62 g).

[0445] 

(2) The compound obtained in (1) mentioned above (4.62 g) was dissolved in chloroform (25 ml), the solution was added with 37% aqueous formaldehyde (2.2 ml) and sodium triacetoxyborohydride (1.38 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a 10a-N-methyl compound (4.55 g).

[0446] 

(3) The compound obtained in (2) mentioned above (4.55 g) was dissolved in tetrahydrofuran (20 ml), the solution was added with triethylamine (469 mg) and 2,4,6-trichlorobenzoyl chloride (1.13 g), and the mixture was stirred at room temperature for 3 hours. This solution was added dropwise to a solution of 4-dimethylaminopyridine (12.9 g) in acetonitrile (420 ml) under reflux by heating. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 65:5:0.1) to obtain a cyclized compound (2.46 g).

[0447] 

(4) The compound obtained in (3) mentioned above (600 mg) was dissolved in tetrahydrofuran (10 ml), the solution was added with a hydrogen fluoride-pyridine complex (161 mg), and the mixture was stirred at room temperature for 15 hours.
The reaction mixture was saturated neutralized with aqueous sodium hydrogencarbonate, and then added with 10% aqueous sodium hydroxide and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 1 (311 mg).

Example 8

[0448] 

(1) The compound obtained in Example 1 (1.06 g) was dissolved in toluene (10 ml), the solution was added with triethylamine (866 mg) and 2-bromoethanol (666 mg), and the mixture was stirred for 2 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 25:1:0.1) to obtain a 10a-(N-2-hydroxyethyl) compound (1.49 g).

(2) By using the compound obtained in (1) mentioned above (1.49 g) as a starting material, the compound shown in Table 1 (135 mg) was obtained in the same manners as those of Example 7, (2), (3) and (4).

Example 9

[0449] By using the compound obtained in Example 1 (1.0 g) and benzyl (S)-(+)-glycidyl ether (0.83 g) as starting materials, the compound shown in Table 1 (89 mg) was obtained in the same manner as that of Example 7.

Example 10

[0450] By using the compound obtained in Example 1 (700 mg) and (S)-1,2-epoxybutane (254 mg) as starting materials, the compound shown in Table 1 (21.6 mg) was obtained in the same manner as that of Example 7.

Example 11

[0451] By using the compound obtained in Example 1 (1.0 g) and (S)-glycidyl methyl ether (266 mg) as starting materials, the compound shown in Table 1 (80 mg) was obtained in the same manner as that of Example 7.

Example 12

[0452] By using the compound obtained in Example 1 (0.5 g) and (R)-(+)-propylene oxide (0.18 ml) as starting materials, the compound shown in Table 1 (10.9 mg) was obtained in the same manner as that of Example 7.

Example 13

[0453] By using the compound obtained in Example 1 (1.0 g) and 1,2-epoxypentane (434 mg) as starting materials, the compound shown in Table 1 (51 mg) was obtained in the same manner as that of Example 7.

Example 14

[0454] By using the compound obtained in Example 1 (1.0 g) and 1,2-epoxypentane (434 mg) as starting materials, the compound shown in Table 1 (5 mg) was obtained in the same manner as that of Example 7.

Example 15

[0455] By using the compound obtained in Example 1 (0.5 g) and (R)-(+)-1,2-epoxyhexane (0.303 ml) as starting materials, the compound shown in Table 1 (32.8 mg) was obtained in the same manner as that of Example 7.

Example 16

[0456] By using the compound obtained in Example 1 (1.0 g) and benzyl (R)-(-)-glycidyl ether (0.83 g) as starting materials, the compound shown in Table 1 (12.5 mg) was obtained in the same manner as that of Example 7.

Example 17

[0457] 

(1) By using the compound obtained in Example 1 (2.0 g) and the compound obtained in Reference Example 1 (2.78 g) as starting materials, a 10a-N-methyl compound (406 mg) was obtained in the same manners as those of Example 7, (1) and (2).

(2) By using the compound obtained in (1) mentioned above (200 mg) as a starting material, a cyclized compound (78 mg) was obtained in the same manner as that of Example 7, (3).

(3) By using the compound obtained in (2) mentioned above (78 mg) as a starting material, the compound shown in Table 1 (52.3 mg) was obtained in the same manner as that of Example 7, (4).

Example 18

[0458] By using the compound obtained in Example 1 (2.0 g) and the compound obtained in Reference Example 1 (2.78 g) as starting materials, the compound shown in Table 1 (31.3 mg) was obtained in the same manner as that of Example 7.

Example 19

[0459] By using the compound obtained in Example 1 (1.5 g) and N-glycidylpyrrole (0.93 g) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 49-017899) as starting materials, the compound shown in Table 1 (102.3 mg) was obtained in the same manner as that of Example 7.

Example 20

[0460] By using the compound obtained in Example 1 (1.5 g) and N-glycidylpyrrole (0.93 g) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 49-017899) as starting materials, the compound shown in Table 1 (2.7 mg) was obtained in the same manner as that of Example 7.

Example 21

[0461] 

(1) The compound obtained in Example 17, (1) (0.2 g) was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (50 mg), and the mixture was stirred at room temperature for 1 day under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (50 mg), and the mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure to obtain a debenzyloxycarbonylated compound (167 mg).

[0462] 

(2) The compound obtained in (1) mentioned above (161 mg) was dissolved in chloroform (5 ml), the solution was added with 37% aqueous formaldehyde (0.12 ml) and sodium triacetoxyborohydride (95 mg), and the mixture was stirred at room temperature for 1.5 hours. The mixture was further added with 37% aqueous formaldehyde (0.12 ml) and sodium triacetoxyborohydride (95 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure to obtain a dimethylamino compound (201 mg).

[0463] 

(3) By using the compound obtained in (2) mentioned above (201 mg) as a starting material, the compound shown in Table 1 (25.3 mg) was obtained in the same manners as those of Example 7, (3) and (4).

Example 22

[0464] By using the compound obtained in Example 1 (1.0 g) and 4-(2,3-epoxypropyl)morpholine (0.43 g) as starting materials, the compound shown in Table 1 (42.0 mg) was obtained in the same manner as that of Example 7.

Example 23

[0465] 

(1) By using the compound obtained in Example 1 (2.33 g) and the compound obtained in Reference Example 2 (2.0 g) as starting materials, a cyclized compound (859 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) Tri-O-tolylphosphine (20.1 mg) was dissolved in toluene (4 ml), the solution was successively added with tris(dibenzylideneacetone)dipalladium(0) (30.2 mg), tri-n-butyl(2-furyl)tin (236 mg) and a solution of the compound obtained in (1) mentioned above (420 mg) in toluene (13 ml), and the mixture was stirred for 1.5 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain an biaryl compound (403 mg).

(3) By using the compound obtained in (2) mentioned above (403 mg) as a starting material, the compound shown in Table 1 (264 mg) was obtained in the same manner as that of Example 7, (4).

Example 24

[0466] By using the compound obtained in Example 1 (553 mg) and the compound obtained in Reference Example 3 (950 mg) as starting materials, the compound shown in Table 1 (4.5 mg) was obtained in the same manners as those of Example 23 (Example 7, (1), (2) and (3), Example 23, (2) and Example 7, (4)).

Example 25

[0467] 

(1) By using the compound obtained in Example 1 (3.63 g) and 2-(2-azidoethyl)oxirane (4.14 g) obtained by the method described in the literature (Tetrahedron, 1987, vol. 43, p.1799) as starting materials, a cyclized compound (468 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

[0468] 

(2) The compound obtained in (1) mentioned above (0.1 g) was dissolved in chloroform (3 ml), the solution was added with a 1 M solution of trimethylphosphine in tetrahydrofuran (0.18 ml) under ice cooling, and the mixture was stirred at room temperature for 1.5 hours. A solution of 2-(1,2-benzisoxazol-3-yl)acetic acid (24.1 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (26.1 mg) and 1-hydroxybenzotriazole monohydrate (20.8 mg) in chloroform (3 ml) separately stirred at room temperature for 1.5 hours was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hours. A solution (2 ml) of 2-(1,2-benzisoxazol-3-yl)acetic acid (24.1 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (26.1 mg) and 1-hydroxybenzotriazole monohydrate (20.8 mg) in chloroform separately stirred at room temperature for 1.5 hours was added to the reaction mixture, and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain an amide compound (20.0 mg).

[0469] 

(3) By using the compound obtained in (2) mentioned above (20.0 mg) as a starting material, the compound shown in Table 1 (13.1 mg) was obtained in the same manner as that of Example 7, (4).

Example 26

[0470] 

(1) By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 5 (0.43 g) as starting materials, a cyclized compound (231 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (70 mg) as a starting material, the compound shown in Table 1 (25.0 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 27

[0471] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 6 (0.43 g) as starting materials, the compound shown in Table 1 (35.3 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 28

[0472] By using the compound obtained in Example 23, (1) (70 mg) and tri-n-butyl-(2-pyridyl)tin (30.3 mg) as starting materials, the compound shown in Table 1 (23.2 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 29

[0473] By using the compound obtained in Example 23, (1) (70 mg) and tri-n-butyl-(3-pyridyl)tin (30.3 mg) as starting materials, the compound shown in Table 1 (20.5 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 30

[0474] By using the compound obtained in Example 1 (433 mg) and the compound obtained in Reference Example 7 (390 mg) as starting materials, the compound shown in Table 1 (44.2 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 31

[0475] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 8 (0.41 g) as starting materials, the compound shown in Table 1 (23.3 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 32

[0476] By using the compound obtained in Example 1 (866 mg) and the compound obtained in Reference Example 9 (1.30 g) as starting materials, the compound shown in Table 1 (35.9 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 33

[0477] By using the compound obtained in Example 1 (909 mg) and the compound obtained in Reference Example 10 (1.30 g) as starting materials, the compound shown in Table 1 (57.2 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 34

[0478] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 11 (0.43 g) as starting materials, the compound shown in Table 1 (24.0 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 35

[0479] By using the compound obtained in Example 1 (793 mg) and the compound obtained in Reference Example 12 (680 mg) as starting materials, the compound shown in Table 1 (96.5 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 36

[0480] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 13 (0.39 g) as starting materials, the compound shown in Table 1 (104.6 mg) was obtained in the same manner as that of Example 7.

Example 37

[0481] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 14 (0.43 g) as starting materials, the compound shown in Table 1 (29.8 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 38

[0482] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 15 (0.43 g) as starting materials, the compound shown in Table 1 (68.2 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 39

[0483] By using the compound obtained in Example 1 (1.0 g) and allyl glycidyl ether (0.57 g) as starting materials, the compound shown in Table 1 (85.0 mg) was obtained in the same manner as that of Example 7.

Example 40

[0484] By using the compound obtained in Example 1 (1.0 g) and propargyl glycidyl ether (0.54 ml) as starting materials, the compound shown in Table 1 (95.3 mg) was obtained in the same manner as that of Example 7.

Example 41

[0485] Palladium(II) acetate (1.2 mg) was dissolved in 1,2-dimethoxyethane (2 ml), the solution was successively added with triphenylphosphine (5.5 mg) and the compound obtained in Reference Example 16 (17.6 mg) under a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was successively added with the compound obtained in Example 39 (40 mg), tetrabutylammonium bromide (33.9 mg) and diisopropylethylamine (18.8 µl) under a nitrogen atmosphere, and the mixture was stirred for 5 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (ethyl acetate:methanol:28% aqueous ammonia = 5:1:0.1) to obtain the compound shown in Table 1 (2.3 mg).

Example 42

[0486] The compound obtained in Example 40 (85 mg) was dissolved in acetonitrile (3 ml), the solution was successively added with the compound obtained in Reference Example 16 (37.5 mg), triethylamine (1 ml), and tetrakistriphenylphosphine palladium (6.5 mg), and the mixture was stirred for 2.5 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 1 (43.2 mg).

Example 43

[0487] The compound obtained in Example 42 (30 mg) was dissolved in methanol (1.5 ml), the solution was added with 5% palladium-carbon (6 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 1 (22.9 mg).

Example 44

[0488] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 17 (943 mg) as starting materials, the compound shown in Table 1 (19 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 45

[0489] By using the compound obtained in Example 1 (0.3 g) and the compound obtained in Reference Example 18 (0.23 g) as starting materials, the compound shown in Table 1 (14 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 46

[0490] By using the compound obtained in Example 1 (0.3 g) and the compound obtained in Reference Example 19 (0.245 g) as starting materials, the compound shown in Table 1 (12 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 47

[0491] 

(1) By using the compound obtained in Example 1 (2.33 g) and the compound obtained in Reference Example 15 (2.0 g) as starting materials, a cyclized compound (0.37 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (30 mg) and tri-n-butyl-(2-pyridyl)tin (13.0 mg) as starting materials, the compound shown in Table 1 (6.1 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 48

[0492] By using the compound obtained in Example 47, (1) (30 mg) and tri-n-butyl-(3-pyridyl)tin (13.0 mg) as starting materials, the compound shown in Table 1 (1.2 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 49

[0493] 

(1) Palladium(II) acetate (0.5 mg) was dissolved in 1,2-dimethoxyethane (0.3 ml), and the solution was successively added with triphenylphosphine (3.1 mg) and quinoline-3-boronic acid (6.1 mg) under a nitrogen atmosphere. The mixture was successively added with sodium carbonate (5.0 mg), distilled water (0.5 ml), and a solution of the compound obtained in Example 47, (1) (30 mg) in 1,2-dimethoxyethane (0.2 ml), and the mixture was stirred at 80°C for 2 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a biaryl compound (12.6 mg).

(2) By using the compound obtained in (1) mentioned above (12.6 mg) as a starting material, the compound shown in Table 1 (3.8 mg) was obtained in the same manner as that of Example 7, (4).

Example 50

[0494] By using the compound obtained in Example 1 (0.33 g) and the compound obtained in Reference Example 20 (0.30 g) as starting materials, the compound shown in Table 1 (19.2 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 51

[0495] 

(1) By using the compound obtained in Example 1 (9.59 g) and the compound obtained in Reference Example 21 (7.36 g) as starting materials, a cyclized compound (895 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) From the compound obtained in (1) mentioned above (50 mg), an azide compound (37 mg) was obtained in the same manner as that of Example 7, (4).

(3) The compound obtained in (2) mentioned above (32 mg) was dissolved in methanol, the solution was added with 5% palladium-carbon (30 mg), and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form silica gel, chloroform:methanol = 50:1) to obtain the compound shown in Table 1 (21.5 mg).

Example 52

[0496] 

(1) By using the compound obtained in Example 1 (1.21 g) and (R)-epichlorohydrin as starting materials, a chloromethyl compound (130 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (25 mg) as a starting material, the compound shown in Table 1 (15 mg) was obtained in the same manner as that of Example 7, (4).

Example 53

[0497] By using the compound obtained in Example 47, (1) (30 mg) and tri-n-butyl-(2-thienyl)tin (13.2 mg) as starting materials, the compound shown in Table 1 (11.4 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 54

[0498] 

(1) The compound obtained in Example 51, (1) (50 mg) was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (10 mg), and the mixture was stirred at room temperature for 1 day under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure to obtain an amine compound (55 mg).

[0499] 

(2) (Method A)
The compound obtained in (1) mentioned above (15 mg) was dissolved in tetrahydrofuran (0.5 ml), the solution was added with 4-dimethylaminopyridine (1.7 mg) and N,N'-carbonyldiimidazole (3.3 mg), and the mixture was stirred at room temperature for 30 minutes. The mixture was added with 3-bromophenol (11.9 mg), and the mixture was stirred for 5 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with toluene (5 ml), and the mixture was stirred for 7 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a carbamate compound (8.0 mg).

(3) (Method B)
The compound obtained in (1) mentioned above (15 mg) was dissolved in chloroform (0.4 ml), and the solution was added with saturated aqueous sodium hydrogencarbonate (0.2 ml). Then, the mixture was added with triphosgene (4.1 mg) under ice cooling, and the mixture was stirred for 30 minutes. The layers of the reaction mixture were separated, and the organic layer was concentrated under reduced pressure. The resulting residue was dissolved in toluene (0.5 ml), the solution was added with 3-bromophenol (11.9 mg), and the mixture was stirred at 85°C for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a carbamate compound (6.8 mg).

[0500] 

(4) By using the compound obtained in (2) or (3) mentioned above (15 mg) as a starting material, the compound shown in Table 1 (3.9 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 55

[0501] 

(1) The compound obtained in Example 54, (1) (20 mg) was dissolved in chloroform (0.5 ml), the solution was added with triethylamine (26 µl) and 2-quinolinecarbonyl chloride (17.6 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain an amide compound (19.5 mg).

[0502] 

(2) By using the compound obtained in (1) mentioned above (19.5 mg) as a starting material, the compound shown in Table 1 (11.9 mg) was obtained in the same manner as that of Example 7, (4).

Example 56

[0503] By using the compound obtained in Example 54, (1) (20 mg) and 3-quinolinecarbonyl chloride (17.6 mg) obtained by the method described in the literature (Bioorganic & Medicinal Chemistry, 2005, vol. 13, p.2031) as starting materials, the compound shown in Table 1 (8.0 mg) was obtained in the same manners as those of Example 55, (1) and Example 7, (4).

Example 57

[0504] By using the compound obtained in Example 54, (1) (20 mg) and 4-quinolinecarbonyl chloride (17.6 mg) obtained by the method described in the literature (Bioorganic & Medicinal Chemistry, 2005, vol. 13, p.2031) as starting materials, the compound shown in Table 1 (8.6 mg) was obtained in the same manners as those of Example 55, (1) and Example 7, (4).

Example 58

[0505] By using the compound obtained in Example 1 (2.82 g) and the compound obtained in Reference Example 22 as starting materials, the compound shown in Table 1 (14 mg) was obtained in the same manner as that of Example 7.

Example 59

[0506] 

(1) By using the compound obtained in Example 54, (1) (35 mg) and 4-bromobenzoyl chloride (21.2 mg) as starting materials, an amide compound (44.5 mg) was obtained in the same manner as that of Example 55, (1).

(2) By using the compound obtained in (1) mentioned above (27.6 mg) as a starting material, the compound shown in Table 1 (8.1 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 60

[0507] By using the compound obtained in Example 1 (1.6 g) and the compound obtained in Reference Example 23 (1.44 g) as starting materials, the compound shown in Table 1 (12.6 mg) was obtained in the same manner as that of Example 23 (Example 7, (1), (2), (3), Example 23, (2) and Example 7, (4)).

Example 61

[0508] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 24 (771 mg) as starting materials, the compound shown in Table 1 (8.6 mg) was obtained in the same manner as that of Example 7.

Example 62

[0509] By using the compound obtained in Example 1 (4.89 g) and the compound obtained in Reference Example 25 (3.25 g) as starting materials, the compound shown in Table 1 (8.7 mg) was obtained in the same manner as that of Example 7.

Example 63

[0510] 

(1) By using the compound obtained in Example 1 (1.77 g) and the compound obtained in Reference Example 26 (2.05 g) as starting materials, a cyclized compound (205 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (32.1 mg) as a starting material, the compound shown in Table 1 (15.5 mg) was obtained in the same manner as that of Example 7, (4).

Example 64

[0511] The compound obtained in Example 63 (8.3 mg) was dissolved in ethyl acetate (1.5 ml), the solution was added with 5% palladium-carbon (4.2 mg), and the mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 1 (8.2 mg).

Example 65

[0512] 

(1) By using the compound obtained in Example 1 (2.12 g) and the compound obtained in Reference Example 27 (3.00 g) as starting materials, a cyclized compound (127 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (39.5 mg) as a starting material, the compound shown in Table 1 (21.3 mg) was obtained in the same manner as that of Example 7, (4).

Example 66

[0513] By using the compound obtained in Example 1 (2.0 g) and epifluorohydrin (919 mg) as starting materials, the compound shown in Table 1 (51 mg) was obtained in the same manner as that of Example 7.

Example 67

[0514] By using the compound obtained in Example 1 (2.0 g) and (R)-2-vinyloxirane (460 mg) as starting materials, the compound shown in Table 1 (26 mg) was obtained in the same manner as that of Example 7.

Example 68

[0515] 

(1) By using the compound obtained in Example 1 (0.30 g) and the compound obtained in Reference Example 28 (0.43 g) as starting materials, a cyclized compound (95.3 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (10 mg) as a starting material, the compound shown in Table 1 (7.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 69

[0516] 

(1) By using the compound obtained in Example 1 (0.38 g) and the compound obtained in Reference Example 29 (0.55 g) as starting materials, a cyclized compound (73 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (10 mg) as a starting material, the compound shown in Table 1 (5.3 mg) was obtained in the same manner as that of Example 7, (4).

Example 70

[0517] 

(1) By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 30 (0.76 g) as starting materials, a cyclized compound (45.2 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (10 mg) as a starting material, the compound shown in Table 1 (6.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 71

[0518] 

(1) By using the compound obtained in Example 1 (0.98 g) and the compound obtained in Reference Example 31 as starting materials, a cyclized compound (0.32 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (130 mg) as a starting material, the compound shown in Table 1 (69 mg) was obtained in the same manner as that of Example 7, (4).

Example 72

[0519] By using the compound obtained in Example 1 (375 mg) and 2-[3-(benzyloxy)propyl]oxirane (435 mg) obtained by the method described in the literature (European Journal of Organic Chemistry, 2000, p.1219) as starting materials, the compound shown in Table 1 (32 mg) was obtained in the same manner as that of Example 7.

Example 73

[0520] The compound obtained in Example 72 (28 mg) was dissolved in methanol, the solution was added with 20% palladium hydroxide-carbon (30 mg), and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 1 (26.7 mg).

Example 74

[0521] 

(1) The compound obtained in Example 51, (1) (20 mg) was dissolved in ethyl acetate, the solution was added with 5% palladium-carbon (20 mg), and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in chloroform (1 ml), the solution was added with triethylamine (9.1 mg) and 3-bromobenzenesulfonyl chloride (4.6 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a bromo compound (11.4 mg).

(2) By using the compound obtained in (1) mentioned above (11.4 mg) as a starting material, the compound shown in Table 1 (2.0 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 75

[0522] 

(1) The compound obtained in Example 54, (1) (50 mg) was dissolved in a mixed solvent of chloroform-methanol (2:1, 1.5 ml), the solution was added with 6-bromopicolinic acid (27.8 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (26.3 mg), and 4-dimethylaminopyridine (5.6 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain an amide compound (65.5 mg).

(2) By using the compound obtained in (1) mentioned above (60 mg) as a starting material, the compound shown in Table 1 (38.0 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 76

[0523] By using the compound obtained in Example 54, (1) (50 mg) and 5-bromonicotinic acid (27.8 mg) as starting materials, the compound shown in Table 1 (16.9 mg) was obtained in the same manners as those of Example 75, (1), Example 23, (2) and Example 7, (4).

Example 77

[0524] By using the compound obtained in Example 54, (1) (50 mg) and 5-bromo-2-thiophenecarboxylic acid (28.6 mg) as starting materials, the compound shown in Table 1 (30.8 mg) was obtained in the same manners as those of Example 75, (1), Example 23, (2) and Example 7, (4).

Example 78

[0525] By using the compound obtained in Example 54, (1) (50 mg) and 5-bromo-2-furancarboxylic acid (26.1 mg) as starting materials, the compound shown in Table 1 (21.6 mg) was obtained in the same manners as those of Example 75, (1), Example 23, (2) and Example 7, (4).

Example 79

[0526] 

(1) By using the compound obtained in Example 1 (4.00 g) and the compound (2.16 g) obtained by the method described in the literature (Synthesis, 1992, p.621, Reference Example 32) as starting materials, a cyclized compound (0.78 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (130 mg) as a starting material, the compound shown in Table 1 (68 mg) was obtained in the same manner as that of Example 7, (4).

Example 80

[0527] By using the compound obtained in Example 1 (1.20 g) and the compound obtained in Reference Example 33 as starting materials, the compound shown in Table 1 (73 mg) was obtained in the same manner as that of Example 7.

Example 81

[0528] The compound obtained in Example 71 (12 mg) was dissolved in a mixed solvent of methanol-ethyl acetate(1:1, 2 ml), the solution was added with 20% palladium hydroxide-carbon (12 mg), and the mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1 to 20:1:0.1) to obtain the compound shown in Table 1 (8 mg).

Example 82

[0529] 

(1) By using the compound obtained in Example 1 (4.00 g) and the compound obtained in Reference Example 34 as starting materials, a cyclized compound (0.76 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (0.38 g) as a starting material, the compound shown in Table 1 (0.25 g) was obtained in the same manner as that of Example 7, (4).

Example 83

[0530] By using the compound obtained in Example 1 (1.00 g) and the compound obtained in Reference Example 35 as starting materials, the compound shown in Table 1 (50 mg) was obtained in the same manner as that of Example 7.

Example 84

[0531] By using the compound obtained in Example 79 (40 mg) as a starting material, the compound shown in Table 1 (34 mg) was obtained in the same manner as that of Example 81.

Example 85

[0532] The compound obtained in Example 82 (160 mg) was dissolved in methanol (20 ml), the solution was added with 5% palladium-carbon (160 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 1 (75 mg).

Example 86

[0533] 

(1) By using the compound obtained in Example 1 (4.00 g) and the compound obtained in Reference Example 36 as starting materials, a cyclized compound (0.51 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (96 mg) as a starting material, a deprotected compound (60 mg) was obtained in the same manner as that of Example 7, (4).

(3) By using the compound obtained in (2) mentioned above (34 mg) as a starting material, the compound shown in Table 1 (21 mg) was obtained in the same manner as that of Example 21, (1).

Example 87

[0534] By using the compound obtained in Example 85 (10 mg) as a starting material, the compound shown in Table 1 (6 mg) was obtained in the same manner as that of Example 7, (2).

Example 88

[0535] 

(1) The compound obtained in Example 52, (1) (68 mg) was dissolved in dimethylformamide (2 ml), the solution was added with imidazole (13 mg) and potassium carbonate (26 mg), and the mixture was stirred at 70°C for 5 hours, and further stirred at 120°C for 3 hours. The reaction mixture was added with distilled water and chloroform, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 100:1:0.1) to obtain an imidazolyl compound (18 mg).

(2) By using the compound obtained in (1) mentioned above (18 mg) as a starting material, the compound shown in Table 1 (11 mg) was obtained in the same manner as that of Example 7, (4).

Example 89

[0536] By using the compound obtained in Example 52, (1) (38 mg) and 3-(4,5-dihydroxy-1H-imidazol-4-yl)-pyridine (25 mg) obtained by the method described in the literature (Journal of Medicinal Chemistry, 2005, vol. 48, p.224) as starting materials, the compound shown in Table 1 (6 mg) was obtained in the same manners as those of Example 88, (1) and Example 7, (4).

Example 90

[0537] 

(1) By using the compound obtained in Example 1 (3 g) and methyl-(S)-glycidate (925 mg) as starting materials, a cyclized compound (910 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (30.7 mg) as a starting material, the compound shown in Table 1 (16.2 mg) was obtained in the same manner as that of Example 7, (4).

Example 91

[0538] 

(1) By using the compound obtained in Example 65, (1) (36.5 mg) as a starting material, a carboxylic acid compound (31.6 mg) was obtained in the same manner as that of Example 64.

(2) The compound obtained in (1) mentioned above (10.1 mg) was dissolved in chloroform (1.0 ml), the solution was added with triethylamine (6.2 µl) and isobutyl chloroformate (5.8 µl) under ice cooling, and the mixture was stirred at the same temperature for 1 hour. The mixture was added with a 0.5 N solution of ammonia in 1,4-dioxane, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was neutralized with saturated aqueous ammonium chloride, and then extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 10:10:0.2) to obtain an amide compound (10.5 mg).

(3) By using the compound obtained in (2) mentioned above (10.1 mg) as a starting material, the compound shown in Table 1 (2.8 mg) was obtained in the same manner as that of Example 7, (4).

Example 92

[0539] 

(1) By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 37 (0.64 g) as starting materials, a nitro compound (24.0 mg) was obtained in the same manner as that of Example 7.

(2) The compound obtained in (1) mentioned above (20 mg) was dissolved in a mixed solvent of 2-propanol-distilled water (2:1, 3 ml), the solution was added with iron (12.4 mg) and ammonium chloride (2.4 mg), and the mixture was stirred at 90°C for 1 hour. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 1 (6.5 mg).

Example 93

[0540] By using the compound obtained in Example 1 (0.5 g) and the compound obtained in Reference Example 38 (0.585 g) as starting materials, the compound shown in Table 1 (47.2 mg) was obtained in the same manner as that of Example 7.

Example 94

[0541] By using the compound obtained in Example 69, (1) (30 mg) as a starting material, the compound shown in Table 1 (11 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 95

[0542] 

(1) By using the compound obtained in Example 1 (4.00 g) and 2-(2-azidoethyl)oxirane obtained by the method described in the literature (Tetrahedron, 1987, vol. 43, p.1799) as starting materials, a cyclized compound (0.29 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

[0543] 

(2) The compound obtained in (1) mentioned above (57 mg) was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (57 mg), and the mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (1 ml), the solution was added with phenyl chloroformate (8 µl) and triethylamine (8 µl), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated aqueous sodium hydrogencarbonate and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 25:5:0.1) to obtain a carbamate compound (35 mg).

(3) By using the compound obtained in (2) mentioned above (35 mg) as a starting material, the compound shown in Table 1 (13 mg) was obtained in the same manner as that of Example 7, (4).

Example 96

[0544] By using the compound obtained in Example 68, (1) (20.6 mg) as a starting material, the compound shown in Table 1 (9.1 mg) was obtained in the same manners as those of Example 23, (2) and Example 7, (4).

Example 97

[0545] 

(1) By using the compound obtained in Example 1 (2.41 g) and the compound obtained in Reference Example 39 (2.52 g) as starting materials, a cyclized compound (253 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (21.6 mg) as a starting material, the compound shown in Table 1 (5.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 98

[0546] By using the compound obtained in Example 1 (0.465 g) and the compound obtained in Reference Example 40 (0.39 g) as starting materials, the compound shown in Table 1 (10.8 mg) was obtained in the same manner as that of Example 7.

Example 99

[0547] 

(1) The compound obtained in Example 54, (1) (45 mg) was dissolved in chloroform (4 ml), the solution was added with 4-quinolinecarboxaldehyde (6.5 mg) and sodium triacetoxyborohydride (13.1 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 10:10:0.2) to obtain an N-(4-quinolylmethyl) compound (40.8 mg).

(2) By using the compound obtained in (1) mentioned above (40 mg) as a starting material, the compound shown in Table 1 (14.3 mg) was obtained in the same manner as that of Example 7, (4).

Example 100

[0548] The compound obtained in Example 99 (6.0 mg) was dissolved in chloroform (0.5 ml), the solution was added with 37% aqueous formaldehyde (2.7 µl) and sodium triacetoxyborohydride (2.15 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 1 (1.1 mg).

Example 101

[0549] By using the compound obtained in Example 1 (0.37 g) and the compound obtained in Reference Example 41 (0.45 g) as starting materials, the compound shown in Table 1 (47 mg) was obtained in the same manner as that of Example 7.

Example 102

[0550] By using the compound obtained in Example 1 (693 mg) and oxiran-2-ylacetonitrile (870 mg) obtained by the method described in the literature (Journal of Organic Chemistry, 2001, vol. 66, 6, p.2171) as starting materials, the compound shown in Table 1 (8.0 mg) was obtained in the same manner as that of Example 7.

Example 103

[0551] 

(1) By using the compound obtained in Example 1 (700 mg) and 3-oxiran-2-ylpropanenitrile (2.05 g) obtained by the method described in the literature (Journal of the Chemical Society, Perkin Transactions II, 1987, 9, p.1253) as starting materials, a cyclized compound (122 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (83.0 mg) as a starting material, the compound shown in Table 1 (44.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 104

[0552] 

(1) By using the compound obtained in Example 1 (700 mg) and the compound obtained in Reference Example 42 (2.35 g) as starting materials, a cyclized compound (99.7 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (68.1 mg) as a starting material, the compound shown in Table 1 (33.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 105

[0553] By using the compound obtained in Example 1 (500 mg) and the compound obtained in Reference Example 43 (989 mg) as starting materials, the compound shown in Table 1 (6.4 mg) was obtained in the same manner as that of Example 7.

Example 106

[0554] By using the compound obtained in Example 1 (500 mg) and the compound obtained in Reference Example 44 (1.1 g) as starting materials, the compound shown in Table 1 (21.7 mg) was obtained in the same manner as that of Example 7.

Example 107

[0555] By using the compound obtained in Example 1 (500 mg) and the compound obtained in Reference Example 45 (989 mg) as starting materials, the compound shown in Table 1 (2.75 mg) was obtained in the same manner as that of Example 7.

Example 108

[0556] By using the compound obtained in Example 1 (500 mg) and the compound obtained in Reference Example 46 (1.1 g) as starting materials, the compound shown in Table 1 (28.5 mg) was obtained in the same manner as that of Example 7.

Syntheses of Examples 109 and 110

[0557] Preparation methods of the compounds represented by the formula (C) having R defined in the examples are shown below.

[0558] 

Example 109: Synthesis of the compound of the formula (C) wherein R = hydrogen atom

[0559] By using the compound obtained in Example 2 (780 mg) as a starting material, the title compound (12 mg) was obtained in the same manners as those of Example 8, (1), Example 7, (2), (3) and (4).
MS (ESI) m/z = 677.3 [M+H]⁺

Example 110: Synthesis of the compound of the formula (C) wherein R = ethyl

[0560] By using the compound obtained in Example 2 (0.5 g) and (R)-1,2-epoxybutane as starting materials, the title compound (39 mg) was obtained in the same manner as that of Example 7.
MS (ESI) m/z = 705.4 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.90 (t, J=7.38Hz, 3H), 0.93-1.01 (m, 6H), 1.10 (d, J=7.31Hz, 3H), 1.16-1.72 (m, 15H), 1.19 (d, J=7.15Hz, 3H), 1.29 (d, J=6.22Hz, 3H), 2.03-2.40 (m, 6H), 2.27 (s, 3H), 2.31 (s, 6H), 2.42-2.78 (m, 4H), 3.02 (t, J=8.94Hz, 1H), 3.19-3.27 (m, 1H), 3.31 (s, 1H), 3.31 (s, 3H), 3.51-3.65 (m, 2H), 3.99-4.11 (m, 1H), 4.31-4.36 (m, 1H), 4.50 (d, J=7.31Hz, 1H), 4.73-4.80 (m, 1H), 4.83 (d, J=4.51Hz, 1H), 4.95 (s, 1H)

Syntheses of Examples 111 to 125

[0561] Preparation methods of the compounds represented by the formula (D) having R^1D, R^2D and R^3D defined in Table 2 are shown below.

[Table 2-1]

[0562] 

Table 2

R1D in the compounds represented by the formula (D) is ethyl group except for the compound of Example 113. R1D in the compound of Example 113 is a group represented by the formula:

Example	R2D	R3D	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
111		H	561.3	(500 MHz) : 0.90 (t, J=7.26 Hz, 3 H) 0.97 (d, J=6.12 Hz, 3 H) 1.04 (d, J=6.88 Hz, 6 H) 1.23 (d, J=6.88 Hz, 3 H) 1.22 - 1.75 (m, 6 H) 1.26 (d, J=6.12 Hz, 3 H) 1.26 - 1.29 (m, 3 H) 1.82 - 1.90 (m, 1 H) 2.06 - 2.13 (m, 1 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.45 - 2.64 (m, 3 H) 2.86 - 2.92 (m, 1 H) 3.11 (s, 3 H) 3.26 (dd, J=9.94, 7.65 Hz, 1 H) 3.49 - 3.58 (m, 1 H) 3.84 - 3.94 (m, 2 H) 3.97 - 4.01 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.50 (d, J=7.65 Hz, 1 H) 4.84 - 4.91 (m, 1 H)
112		H	680.6	(300 MHz) : 0.82 - 0.95 (m, 9 H) 0.97 - 1.31 (m, 2 H) 1.02 (d, J=6.84 Hz, 3 H) 1.07 (d, J=7.31 Hz. 3 H) 1.17 (d, J=6.06 Hz, 3 H) 1.26 (s, 3 H) 1.45 - 1.99 (m, 4 H) 2.09 - 2.28 (m, 2 H) 2.30 (s, 6 H) 2.38 (s, 3 H) 2.43 - 2.64 (m, 3 H) 2.77 - 2.88 (m, 1 H) 2.97 - 3.07 (m, 1 H) 3.14 - 3.51 (m, 3 H) 3.21 (s, 3 H) 3.87 (d, J=4.04 Hz, 1 H) 3.89 - 3.98 (m, 2 H) 4.11 (d, J=7.15 Hz, 1 H) 4.69 - 4.78 (m, 1 H) 5.23 - 5.33 (m, 1 H) 7.19 (ddd, J=7.54, 4.90, 1.09 Hz, 1 H) 7.37 (dt, J=7.81, 0.99 Hz, 1 H) 7.67 (td, J=7.69, 1.87 Hz, 1 H) 8.53 (ddd, J=4.90, 1.79, 0.93 Hz, 1 H)

[0563] 

[Table 2-2]

113			758.6	(300 MHz) : 0.77 (d, J=6.53 Hz, 3 H) 0.83 (d, J=7.15 Hz, 3 H) 1.15 - 1.22 (m, 1 H) 1.22 (d, J=6.06 Hz, 3 H) 1.22 - 1.27 (m, 1 H) 1.29 (s, 3 H) 1.30 - 1.38 (m, 6 H) 1.61 - 1.94 (m, 4 H) 2.00 (d, J=15.70 Hz, 1 H) 2.21 - 2.62 (m, 3 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.75 - 2.83 (m, 1 H) 2.83 (s, 3 H) 2.86 - 3.03 (m, 1 H) 3.16 - 3.34 (m, 2 H) 3.36 - 3.57 (m, 3 H) 3.57 (s, 2 H) 3.84 - 4.01 (m, 2 H) 4.41 (d, J=7.31 Hz, 1 H) 4.68 - 4.81 (m, 1 H) 5.88 (t, J=6.06 Hz, 1 H) 6.47 (dd, J=3.42, 1.87 Hz, 1 H) 6.69 (dd, J=3.42, 0.78 Hz, 1 H) 7.14 - 7.21 (m, 1 H) 7.37 (t, 1 H) 7.44 - 7.49 (m, 1 H) 7.55 - 7.63 (m, 2 H)
114		H		(600 MHz): 0.79 - 0.99 (m, 12 H) 1.07 - 1.25 (m, 2 H) 1.12 (d, J=7.34 Hz, 3 H) 1.19 (d, J=5.96 Hz, 3 H) 1.28 (s, 3 H) 1.50 (t, J=7.11 Hz, 3 H) 1.52 - 1.77 (m, 3 H) 1.85 - 1.99 (m, 1 H) 2.08 - 2.28 (m, 3 H) 2.30 (s, 6 H) 2.39 (s, 3 H) 2.44 - 2.62 (m, 2 H) 2.77 - 2.89 (m, 1 H) 2.99 - 3.10 (m, 1 H) 3.14 - 3.31 (m, 5 H) 3.22 - 3.24 (m, 3 H) 3.64 - 3.75 (m, 3 H) 3.87 (s, 1 H) 3.91 (s, 2 H) 4.02 (s, 1 H) 4.21 - 4.35 (m, 2 H) 4.60 - 4.83 (m, 3 H) 5.31 (s, 1 H) 7.26 (t, J=7.11 Hz, 2 H) 7.30 - 7.35 (m, 2 H) 7.37 (s, 1 H) 7.50 (t, J=8.02 Hz, 1 H) 8.20 (dd, J=8.25, 1.38 Hz, 1 H) 8.66 (s, 1 H)
115		H	923.5	(600 MHz): 0.79 - 0.96 (m, 12 H) 1.04 - 1.30 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.15 (d, J=6.42 Hz, 3 H) 1.24 (s, 3 H) 1.36 (t, J=7.11 Hz, 3 H) 1.45 - 1.75 (m, 3 H) 1.86 - 1.96 (m, 1 H) 2.05 - 2.23 (m, 3 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.41 - 2.59 (m, 2 H) 2.76 - 2.86 (m, 1 H) 2.96 - 3.28 (m, 6 H) 3.19 (s, 3 H) 3.60 - 4.07 (m, 4 H) 3.65 - 3.70 (m, 2 H) 3.87 (s, 2 H) 4.17 - 4.24 (m, 2 H) 4.48 (q, J=6.88 Hz, 2 H) 6.26 (d, J=7.79 Hz, 1 H) 7.09 - 7.16 (m, 1 H) 7.17 - 7.35 (m, 5 H) 7.44 (d, J=7.79 Hz, 1 H) 8.10 (d, J=6.42 Hz, 1 H)
116		H	883.4	(600 MHz): 0.76 - 0.96 (m, 12 H) 1.03 - 1.28 (m, 2 H) 1.06 - 1.11 (m, 3 H) 1.15 (d, J=6.42 Hz, 3 H) 1.23 - 1.24 (m, 3 H) 1.46 - 1.72 (m, 3 H) 1.85 - 1.99 (m, 3 H) 2.10 - 2.40 (m, 3 H) 2.25 - 2.29 (m, 6 H) 2.34 - 2.37 (m, 3 H) 2.43 - 2.57 (m, 2 H) 2.76 (t, J=6.42 Hz, 2 H) 2.79 - 2.85 (m, 1 H) 2.98 - 3.24 (m, 4 H) 2.99 - 3.05 (m, 2 H) 3.20 (s, 3 H) 3.28 - 3.33 (m, 2 H) 3.60 - 4.01 (m, 4 H) 3.67 (s, 2 H) 3.84 (s, 2 H) 4.09 (t, J=5.27 Hz, 2 H) 6.49 - 6.64 (m, 2 H) 7.17 - 7.38 (m, 5 H)
117		H	828.4	(600 MHz) : 0.75 - 0.91 (m, 9 H) 0.92 (d, J=6.88 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.09 - 1.19 (m, 2 H) 1.14 (d, J=6.42 Hz, 3 H) 1.24 (s, 3 H) 1.44 - 1.69 (m, 3 H) 1.85 - 1.95 (m, 1 H) 2.06 - 2.28 (m, 3 H) 2.25 (s, 6 H) 2.36 (s, 3 H) 2.43 - 2.57 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.99 - 3.02 (m, 2 H) 3.01 - 3.05 (m, 1 H) 3.11 - 3.24 (m, 3 H) 3.20 (s, 3 H) 3.62 - 3.70 (m, 3 H) 3.78 - 3.89 (m, 2 H) 3.85 (s, 2 H) 3.92 - 4.01 (m, 1 H) 4.06 - 4.09 (m, 2 H) 6.87 - 6.96 (m, 3 H) 7.17 - 7.36 (m, 6 H)
118		H	995.6

[0564] 

[Table 2-3]

119		H	879.4	(600 MHz) : 0.78 (d, J=7.34 Hz, 3 H) 0.81 - 0.89 (m, 6 H) 0.95 (d, J=6.88 Hz, 3 H) 1.02 (d, J=7.34 Hz, 3 H) 1.06 - 1.22 (m, 2 H) 1.11 (d, J=6.42 Hz, 3 H) 1.19 (s, 3 H) 1.44 - 1.53 (m, 2 H) 1.54 - 1.66 (m, 1 H) 1.79 - 1.90 (m, 1 H) 2.01 (s, 1 H) 2.12 - 2.46 (m, 4 H) 2.26 - 2.29 (m, 9 H) 2.73 - 2.83 (m, 1 H) 2.95 - 3.06 (m, 1 H) 3.13 - 3.23 (m, 3 H) 3.19 (s, 3 H) 3.23 - 3.33 (m, 2 H) 3.59 - 3.72 (m, 2 H) 3.73 - 3.85 (m, 2 H) 3.87 - 3.97 (m, 3 H) 4.28 - 4.41 (m, 3 H) 7.07 (d, J=7.34 Hz, 1 H) 7.18 (d, J=7.34 Hz, 1 H) 7.22 - 7.32 (m, 2 H) 7.35 - 7.42 (m, 2 H) 7.44 (t, J=8.02 Hz, 1 H) 7.49 (s, 1 H) 8.09 - 8.14 (m, 1 H) 8.86 - 8.92 (m, 1 H)
120		H		(600 MHz) : 0.80 - 0.90 (m, 12 H) 0.92 (d, J=6.88 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.06 - 1.26 (m, 2 H) 1.15 (d, J=5.96 Hz, 3 H) 1.24 (s, 3 H) 1.49 - 1.69 (m, 5 H) 1.86 - 1.94 (m, 1 H) 2.07 - 2.42 (m, 5 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.43 - 2.56 (m, 2 H) 2.77 - 2.83 (m, 1 H) 2.99 - 3.08 (m, 1 H) 3.17 (dd, J=10.09, 7.34 Hz, 1 H) 3.20 (s, 3 H) 3.35 - 3.41 (m, 2 H) 3.54 - 3.64 (m, 2 H) 3.77 - 3.91 (m, 2 H) 3.95 - 4.03 (m, 1 H) 4.30 (t, J=6.42 Hz, 2 H) 4.66 - 4.70 (m, 1 H) 4.72 (q, J=6.88 Hz, 2 H) 5.24 (br, s., 1 H) 6.52 (d, J=8.25 Hz, 1 H) 6.64 - 6.68 (m, 2 H) 7.11 (t, J=7.57 Hz, 1 H) 7.31 (d, J=7.79 Hz, 1 H) 7.48 (t, J=8.02 Hz, 1 H) 8.17 (d, J=6.88 Hz, 1 H) 8.63 (s, 1 H)
121		H	893.6	(600 MHz) : 0.68 - 1.01 (m, 6 H) 0.75 (d, J=7.34 Hz, 3 H) 0.95 (d, J=6.88 Hz, 3 H) 1.12 - 1.32 (m, 8 H) 1.17 (d, J=5.96 Hz, 3 H) 1.33 - 1.74 (m, 3 H) 1.83 - 2.27 (m, 3 H) 2.26 - 2.37 (m, 9 H) 2.37 - 2.56 (m, 3 H) 2.61 - 2.70 (m, 1 H) 2.98 (d, J=15.13 Hz, 1 H) 3.16 - 3.28 (m, 2 H) 3.21 (s, 3 H) 3.43 - 3.51 (m, 1 H) 3.67 - 3.93 (m, 3 H) 4.15 - 4.30 (m, 3 H) 4.34 (td, J=9.40, 2.29 Hz, 2 H) 4.58 - 4.74 (m, 1 H) 5.08 - 5.28 (m, 1 H) 7.06 (d, J=7.79 Hz, 1 H) 7.33 - 7.41 (m, 5 H) 7.46 (m, 1 H) 7.80 (s, 1 H) 7.86 (d, J=7.79 Hz, 1 H) 8.14 (dd, J=8.25, 1.38 Hz, 1 H) 9.08 (br s, 1 H)
122		H	893.7	(600 MHz) : 0.79 - 0.86 (m, 6 H) 0.86 - 0.90 (m, 6 H) 0.87 (d, J=6.88 Hz, 3 H) 0.99 - 1.18 (m, 2 H) 1.06 (d, J=7.34 Hz, 3 H) 1.13 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.41 - 1.69 (m, 3 H) 1.75 - 1.94 (m, 1 H) 2.05 - 2.30 (m, 3 H) 2.23 - 2.28 (m, 6 H) 2.33 - 2.36 (m, 6 H) 2.41 - 2.56 (m, 2 H) 2.72 - 2.82 (m, 1 H) 2.94 - 3.04 (m, 1 H) 3.04 (t, J=6.88 Hz, 2 H) 3.10 - 3.23 (m, 4 H) 3.17 - 3.19 (m, 3 H) 3.59 - 3.69 (m, 4 H) 3.81 - 3.86 (m, 1 H) 3.98 (s, 1 H) 4.27 - 4.38 (m, 3 H) 7.00 - 7.05 (m, 1 H) 7.16 - 7.28 (m, 2 H) 7.31 (s, 1 H) 7.34 - 7.44 (m, 4 H) 8.08 - 8.12 (m, 1 H) 8.89 - 8.92 (m, 1 H)
123		H	921.7	(600 MHz): 0.79 - 0.93 (m, 9 H) 1.04 - 1.11 (m, 3 H) 1.09 - 1.31 (m, 2 H) 1.12 - 1.20 (m, 6 H) 1.22 - 1.27 (m, 3 H) 1.43 - 1.63 (m, 3 H) 1.86 - 1.94 (m, 1 H) 2.14 (s, 3 H) 2.20 - 2.41 (m, 3 H) 2.21 - 2.31 (m, 6 H) 2.33 - 2.36 (m, 3 H) 2.42 - 2.59 (m, 2 H) 2.73 - 2.83 (m, 1 H) 2.95 - 3.06 (m, 1 H) 3.07 - 3.34 (m, 4 H) 3.19 - 3.20 (m, 3 H) 3.58 - 3.71 (m, 2 H) 3.80 - 3.92 (m, 5 H) 4.01 (s, 1 H) 4.42 - 4.50 (m, 2 H) 4.61 - 4.75 (m, 1 H) 7.09 - 7.15 (m, 1 H) 7.18 - 7.32 (m, 3 H) 7.35 - 7.48 (m, 4 H) 8.09 - 8.16 (m, 1 H) 8.89 - 8.96 (m, 1 H)

[0565] 

[Table 2-4]

124		H	879.6	(600 MHz) : 0.81 - 0.91 (m, 9 H) 0.93 (d, J=6.88 Hz, 3 H) 1.04 - 1.21 (m, 8 H) 1.23 (s, 3 H) 1.44 - 1.69 (m, 5 H) 1.87 - 1.93 (m, 1 H) 2.06 - 2.61 (m, 5 H) 2.24 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.84 (m, 1 H) 3.00 - 3.26 (m, 3 H) 3.20 (s, 3 H) 3.42 (t, J=5.96 Hz, 2 H) 3.51 - 3.61 (m, 3 H) 3.85 - 4.00 (m, 2 H) 4.38 (t, J=5.96 Hz, 2 H) 4.68 - 4.79 (m, 1 H) 4.94 - 5.04 (m, 1 H) 5.15 - 5.27 (m, 1 H) 6.60 (t, J=6.65 Hz, 2 H) 6.71 (s, 1 H) 7.07 (t, J=7.79 Hz, 2 H) 7.38 - 7.41 (m, 1 H) 7.42 - 7.44 (m, 1 H) 7.45 (t, J=4.13 Hz, 1 H) 8.13 (dd, J=8.48, 1.60 Hz, 1 H) 9.01 (dd, J=4.13, 1.83 Hz, 1 H)
125		H	680.6	(600 MHz) : 0.78 - 0.92 (m, 9 H) 0.95 (d, J=6.88 Hz, 3 H) 1.03 - 1.20 (m, 2 H) 1.08 (d, J=7.34 Hz, 3 H) 1.15 (d, J=5.96 Hz, 3 H) 1.25 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.57 - 1.72 (m, 2 H) 1.82 - 1.93 (m, 1 H) 2.09 - 2.23 (m, 2 H) 2.30 (s, 3 H) 2.37 (s, 6 H) 2.43 - 2.58 (m, 3 H) 2.80 - 2.88 (m, 1 H) 2.96 - 3.07 (m, 1 H) 3.10 - 3.26 (m, 3 H) 3.19 (s, 3 H) 3.70 (d, J=2.29 Hz, 2 H) 3.77 - 3.86 (m, 1 H) 3.94 - 4.09 (m, 1 H) 4.62 - 4.77 (m, 1 H) 5.18 - 5.46 (m, 1 H) 7.27 (dd, J=7.79, 5.04 Hz, 1 H) 7.71 (d, J=7.79 Hz, 1 H) 8.52 (dd, J=4.81, 1.60 Hz, 1 H) 8.54 (d, J=2.29 Hz, 1 H)

Example 111

[0566] The compound obtained in Example 7, (3) (5.35 g) was dissolved in ethanol (20 ml) and 1 N hydrochloric acid (20 ml), and the solution was stirred at room temperature for 2 days. The reaction mixture was neutralized with 10% aqueous sodium hydroxide, and then added with ethyl acetate, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 2 (3.87 g).

Example 112

[0567] 

(1) The compound obtained in Example 111 (3.86 g) was dissolved in acetone (20 ml), the solution was added with acetic anhydride (617 mg), and the mixture was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a 2'-O-acetyl compound (1.81 g) as a crude product. The resulting crude product (1.81 g) was dissolved in dimethylformamide, the solution was added with imidazole (714 mg) and triethylchlorosilane (543 mg), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was washed successively with saturated aqueous ammonium chloride and distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a 2'-O-acetyl-9-O-triethylsilyl-3-hydroxy compound (1.09 g).

[0568] 

(2) The compound obtained in (1) mentioned above (46 mg) was dissolved in toluene (1 ml), the solution was added with 2-pyridylacetic acid hydrochloride (66 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (74 mg) and 4-dimethylaminopyridine (16 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in methanol (2 ml), and the solution was stirred at room temperature for 30 hours. The reaction mixture was concentrated under reduced pressure to obtain a condensed compound.

[0569] 

(3) By using the compound obtained in (2) mentioned above as a starting material, the compound shown in Table 2 (19 mg) was obtained in the same manner as that of Example 7, (4).

Example 113

[0570] 

(1) By using the compound obtained in Example 23, (2) (0.7 g) as a starting material, a 2'-O-acetyl-9-O-triethylsilyl-3-hydroxy compound (114 mg) was obtained in the same manners as those of Example 111 and Example 112, (1).

[0571] 

(2) N-Chlorosuccinimide (146 mg) was dissolved in toluene (3 ml), the solution was added with dimethyl sulfide (0.16 ml) at -20°C, and the mixture was stirred at the same temperature for 10 minutes. The filtrate was added with a solution (3 ml) of the compound obtained in (1) mentioned above (100 mg) in toluene, and the mixture was stirred at the same temperature for 10 minutes. The mixture was added with triethylamine (0.30 ml), and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain a 3-ketone compound (105 mg)

[0572] 

(3) The compound obtained in (2) mentioned above (93 mg) was dissolved in methanol (5 ml), and the solution was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in ethanol (1 ml). The solution was added with 1 N hydrochloric acid (1 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1 to 10:1:0.1) and preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 2 (34.2 mg).

Example 114

[0573] 

(1) The compound obtained in Example 112, (1) (250 mg) was dissolved in toluene (1 ml), the solution was added with the compound obtained in Reference Example 47 (262 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (201 mg) and 4-dimethylaminopyridine (43 mg), and the mixture was stirred at room temperature for 1 day. The mixture was further added with dichloromethane (5 ml), and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain a 3-O-acyl compound (123 mg).

[0574] 

(2) The compound obtained in (1) mentioned above (120 mg) was dissolved in ethanol (2 ml), the solution was added with 1 N hydrochloric acid (2 ml), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with 1 N aqueous sodium hydroxide and ethyl acetate. The layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain an aldehyde compound (39 mg).

[0575] 

(3) The compound obtained in (2) mentioned above (38 mg) was dissolved in a mixed solvent of chloroform-dimethylformamide (3:2, 2.5 ml), the solution was added with a solution (0.5 ml) of 8-(2-aminoethoxy)-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid hydrochloride (48 mg) obtained by the method described in the patent document (WO04/101584) in dimethylformamide and sodium triacetoxyborohydride (32 mg), and the mixture was stirred at room temperature for 18 hours. The mixture was further added with a solution (0.5 ml) of 8-(2-aminoethoxy)-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride (25 mg) in dimethylformamide and sodium triacetoxyborohydride (16 mg), and the mixture was stirred for 4 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and 1 N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain a 2'-acetyl compound (17.3 mg).

[0576] 

(4) The compound obtained in (3) mentioned above (14.4 mg) was dissolved in methanol (0.8 ml), and the solution was stirred at room temperature for 3.5 days.
The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 10:1 to chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 2 (6.8 mg).

Example 115

[0577] 

(1) The compound obtained in Example 114, (2) (0.34 g) was dissolved in methanol (50 ml), and the solution was stirred at 70°C for 2 hours, and further stirred at room temperature for 9 hours. The reaction mixture was concentrated under reduced pressure to obtain a deprotected compound (0.31 g).

[0578] 

(2) The compound obtained in (1) mentioned above (50 mg) was dissolved in dimethylformamide (1.3 ml) and methanol (1.3 ml), the solution was added with the compound obtained in Reference Example 48 (16.2 mg) and acetic acid (0.15 ml), and the mixture was stirred at room temperature for 40 minutes. The mixture was added with sodium cyanoborohydride (13 mg), and the mixture was stirred at room temperature for 6 hours. The mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0.1) to obtain the compound shown in Table 2 (22 mg).

Example 116

[0579] By using the compound obtained in Example 115, (1) (50 mg) and the compound obtained in Reference Example 49 (19 mg) as starting materials, the compound shown in Table 2 (26 mg) was obtained in the same manner as that of Example 115, (2).

Example 117

[0580] By using the compound obtained in Example 115, (1) (50 mg) and the compound obtained in Reference Example 50 (12.3 mg) as starting materials, the compound shown in Table 2 (26 mg) was obtained in the same manner as that of Example 115, (2).

Example 118

[0581] By using the compound obtained in Example 115, (1) (20 mg) and the compound obtained in Reference Example 51 (8.6 mg) as starting materials, the compound shown in Table 2 (1.9 mg) was obtained in the same manner as that of Example 115, (2).

Example 119

[0582] By using the compound obtained in Example 115, (1) (14.9 mg) and the compound obtained in Reference Example 52 (4.0 mg) as starting materials, the compound shown in Table 2 (11.2 mg) was obtained in the same manner as that of Example 115, (2).

Example 120

[0583] 

(1) By using the compound obtained in Example 112, (1) (200 mg) and 3-nitrophenylacetic acid (152 mg) as starting materials, a nitrophenylacetic acid ester compound (266 mg) was obtained in the same manner as that of Example 114, (1).

[0584] 

(2) The compound obtained in (1) mentioned above (260 mg) was dissolved in methanol, and the solution was stirred for 3 hours under reflux by heating. The reaction mixture was left to cool, and then added with 5% palladium-carbon (100 mg), and the mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain an amine compound (180 mg).

[0585] 

(3) The compound obtained in (2) mentioned above (116 mg) was dissolved in methanol (4 ml), the solution was added with the compound obtained in Reference Example 53 (140 mg), sodium acetate (12 mg) and acetic acid (41 µl), and the mixture was stirred at room temperature for 15 minutes. The mixture was added with sodium cyanoborohydride (18 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain an adduct compound (106 mg).

[0586] 

(4) The compound obtained in (3) mentioned above (70 mg) was dissolved in 1 N hydrochloric acid (1 ml) and ethanol (0.1 ml), and the solution was stirred at 80°C for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol = 10:1 to chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 2 (7.8 mg).

Example 121

[0587] 

(1) The compound obtained in Example 114, (2) (63 mg) and sulfamic acid (21 mg) were dissolved in tetrahydrofuran (2 ml), the solution was added with an aqueous solution (2 ml) of sodium chlorite (19 mg), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a carboxyl compound (62 mg).

[0588] 

(2) The compound obtained in (1) mentioned above (62 mg) and the compound obtained in Reference Example 52 (31 mg) were dissolved in dichloromethane (5 ml), the solution was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (31 mg), 1-hydroxybenzotriazole monohydrate (11 mg) and triethylamine (34 µl), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in methanol (50 ml), and the solution was stirred at 80°C for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 2 (12 mg).

Example 122

[0589] By using the compound obtained in Example 119 (5.0 mg) as a starting material, the compound shown in Table 2 (6.5 mg) was obtained in the same manner as that of Example 7, (2).

Example 123

[0590] 

(1) By using the compound obtained in Example 114, (2) (60 mg) and the compound obtained in Reference Example 52 (15.1 mg) as starting materials, a 2'-acetyl compound (9.0 mg) was obtained in the same manner as that of Example 115, (2).

(2) The compound obtained in (1) mentioned above (6 mg) was dissolved in chloroform (0.5 ml), the solution was added with acetic anhydride (0.61 µl), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain an N-acyl compound (7.3 mg).

(3) The compound obtained in (2) mentioned above (7.3 mg) was dissolved in methanol (0.5 ml), and the solution was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 2 (4.5 mg).

Example 124

[0591] By using 3-(quinoline-8-yloxy)propanal (10 mg) obtained from 8-quinolinol in the same manner as that of Reference Example 53 and the compound obtained in Example 120, (2) (35 mg) as starting materials, the compound shown in Table 2 (3.6 mg) was obtained in the same manners as those of Example 120, (3) and (4).

Example 125

[0592] 

(1) By using the compound obtained in Example 112, (1) (97 mg) and 3-pyridylacetic acid hydrochloride as starting materials, an acyl compound (94 mg) was obtained in the same manner as that of Example 112, (2).

(2) The compound obtained in (1) mentioned above (94 mg) was dissolved in ethanol (1 ml), the solution was added with 1 N hydrochloric acid (1 ml), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1 to 10:1:0.1) to obtain a 2'-O-acetyl compound (74 mg).

(3) The compound obtained in (2) mentioned above (23 mg) was dissolved in methanol (5 ml), and the solution was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the compound shown in Table 2 (22 mg).

Syntheses of Examples 126 to 171

[0593] Preparation methods of the compounds of the formula (E) having R^1E, R^2E and R^3E defined in Table 3 are shown below.

[Table 3-1]

[0594] 

Table 3

Example	R1E	R2E	R3E	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
126	Et		H	968.0	(600 MHz) : 0.78 - 0.85 (m, 6 H) 0.86 - 0.95 (m, 6 H) 1.08 - 1.35 (m, 20 H) 1.31 (s, 3 H) 1.49 - 1.88 (m, 5 H) 2.09 - 2.67 (m, 10 H) 2.24 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.94 (m, 1 H) 3.15 - 3.46 (m, J=54.56 Hz, 4 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.53 - 3.60 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.84 (s, 3 H) 4.18 - 4.25 (m, 1 H) 4.32 - 4.46 (m, 3 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.95 - 4.99 (m, 1 H) 5.56 (s, 1 H) 6.84 - 6.94 (m, 2 H) 7.18 - 7.30 (m, 2 H)
127	Et			717.3	(300 MHz) : 0.84 (t, 6 H) 0.92 (t, J=7.46 Hz, 3 H) 1.08 (d, J=7.31 Hz, 3 H) 1.12 - 1.32 (m, 2 H) 1.18 (d, J=7.46 Hz, 3 H) 1.22 (d, J=6.06 Hz, 3 H) 1.30 (s, 3 H) 1.38 (d, J=6.84 Hz, 3 H) 1.43 (s, 3 H) 1.52 - 1.96 (m, 5 H) 2.08 - 2.56 (m, 5 H) 2.28 (s, 6 H) 2.32 (d, J=6.99 Hz, 1 H) 2.38 (s, 3 H) 2.76 - 2.96 (m, 2 H) 3.18 - 3.28 (m, 1 H) 3.24 (s, 3 H) 3.30 (s, 3 H) 3.30 - 3.51 (m, 2 H) 3.71 (d, J=6.84 Hz, 1 H) 4.25 - 4.32 (m, 2 H) 4.49 - 4.60 (m, 1 H) 4.62 - 4.75 (m, 1 H) 5.26 (t, J=7.07 Hz, 1 H)
128	Et			732.5	(300 MHz) : 0.80 - 0.95 (m, 9 H) 1.06 (d, J=7.31 Hz, 3 H) 1.12 - 1.26 (m, 2 H) 1.18 (d, J=6.99 Hz, 3 H) 1.22 (d, J=6.06 Hz, 3 H) 1.29 (s, 3 H) 1.48 (d, J=6.99 Hz, 3 H) 1.52 (s, 3 H) 1.53 - 1.73 (m, 4 H) 1.85 - 1.97 (m, 1 H) 2.09 - 2.37 (m, 4 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.43 - 2.57 (m, 2 H) 2.81 - 2.89 (m, 1 H) 2.91 - 3.00 (m, 1 H) 3.16 - 3.29 (m, 2 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.43 - 3.59 (m, 1 H) 3.83 - 3.96 (m, 1 H) 3.97 - 4.05 (m, 1 H) 4.43 (d, J=7.62 Hz, 1 H) 4.66 - 4.79 (m, 1 H) 5.01 - 5.11 (m, 1 H) 5.16 - 5.28 (m, 1 H)
129	Et		H	718.4	mixture of diastereomers (300 MHz) : 0.73 - 0.97 (m, 9 H) 1.01 - 1.35 (m, 20 H) 1.44 - 1.94 (m, 3 H) 1.98 - 2.61 (m, 7 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.72 - 2.97 (m, 3 H) 3.16 - 3.28 (m, 1 H) 3.25 (s, 3 H) 3.28 - 3.36 (m, 3 H) 3.37 - 3.59 (m, 2 H) 3.68 - 3.77 (m, 1 H) 3.98 - 4.21 (m, 2 H) 4.35 - 4.51 (m, 1 H) 4.59 - 4.73 (m, 2 H) 4.90 - 5.01 (m, 1 H)
		H

[0595] 

[Table 3-2]

130	Et		H	1096.5	(300 MHz) : 0.79 - 0.99 (m, 9 H) 0.99 - 1.35 (m, 24 H) 1.39 - 1.93 (m, 5 H) 2.13 - 2.51 (m, J=16.32 Hz, 5 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.52 - 2.93 (m, 5 H) 3.17 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.38 - 3.47 (m, 1 H) 3.55 - 3.74 (m, 3 H) 3.88 - 3.99 (m, 4 H) 4.14 - 4.20 (m, 1 H) 4.29 - 4.35 (m, 2 H) 4.36 - 4.47 (m, 1 H) 4.52 (d, J=6.06 Hz, 1 H) 4.66 - 4.72 (m, 1 H) 4.73 (d, J=9.64 Hz, 1 H) 5.00 (d, J=5.13 Hz, 1 H) 7.91 (s, 1 H) 8.15 (s, 1 H) 8.84 (s, 1 H)
131	Et		H	1095.5	(300 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.90 (t, J=7.38 Hz, 3 H) 0.94 - 1.92 (m, 23 H) 1.11 (s, 3 H) 1.29 (s, 3 H) 2.12 - 2.93 (m, J=15.23 Hz, 10 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 3.16 - 3.60 (m, 6 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.69 (d, J=7.46 Hz, 1 H) 3.75 - 3.85 (m, 4 H) 4.16 - 4.20 (m, 1 H) 4.39 - 4.45 (m, 1 H) 4.50 (d, J=7.15 Hz, 1 H) 4.64 - 4.70 (m, 1 H) 4.73 (d, J=9.95 Hz, 1 H) 4.97 - 5.06 (m, 2 H) 7.54 (s, 1 H) 8.05 (s, 1 H) 8.74 (s, 1 H)
132	Et		H	953.7	(600 MHz): 0.77 - 0.85 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.99 (t, J=7.11 Hz, 3 H) 1.06 - 1.21 (m, 2 H) 1.10 - 1.18 (m, 15 H) 1.29 - 1.30 (m, 3 H) 1.48 - 1.65 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.79 - 1.89 (m, 1 H) 2.11 - 2.31 (m, 3 H) 2.25 - 2.27 (m, 6 H) 2.35 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.45 - 2.64 (m, 4 H) 2.66 - 2.77 (m, 2 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.92 (m, 1 H) 3.16 - 3.45 (m, 4 H) 3.22 - 3.23 (m, 3 H) 3.31 - 3.32 (m, 3 H) 3.55 - 3.60 (m, 1 H) 3.60 - 3.63 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.73 - 3.76 (m, 1 H) 3.83 (s, 3 H) 4.20 (s, 1 H) 4.34 - 4.42 (m, 1 H) 4.44 (d, J=6.42 Hz, 1 H) 4.54 (d, J=10.09 Hz, 1 H) 4.64 (s, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 5.51 - 5.57 (m, 1 H) 6.85 (d, J=8.25 Hz, 1 H) 6.89 (t, J=7.57 Hz, 1 H) 7.18 - 7.29 (m, 2 H)
133	Et		H	924.5	(300 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.90 (t, J=7.31 Hz, 3 H) 1.01 - 1.37 (m, 17 H) 1.05 (t, J=7.15 Hz, 3 H) 1.31 (s, 3 H) 1.46 - 1.92 (m, 5 H) 2.13 - 2.66 (m, 8 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.66 - 2.94 (m, 4 H) 3.19 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.57 - 3.67 (m, 1 H) 3.71 (d, J=7.31 Hz, 1 H) 3.82 (s, 3 H) 4.09 - 4.22 (m, 2 H) 4.36 - 4.48 (m, 1 H) 4.49 (d, J=7.15 Hz, 1 H) 4.63 - 4.73 (m, 2 H) 4.99 (d, J=4.82 Hz, 1 H) 6.86 (d, J=8.08 Hz, 1 H) 6.95 (t, J=7.46 Hz, 1 H) 7.17 - 7.24 (m, 1 H) 7.30 - 7.35 (m, 1 H)
134	Et		H	952.6	(300 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.90 (t, J=7.46 Hz, 3 H) 0.99 (t, J=6.84 Hz, 3 H) 1.00 - 1.34 (m, 14 H) 1.10 (s, 3 H) 1.12 (d, J=7.15 Hz, 3 H) 1.30 (s, 3 H) 1.46 - 1.91 (m, 5 H) 2.13 - 2.68 (m, 10 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.72 - 3.02 (m, 4 H) 3.20 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.59 - 3.74 (m, 2 H) 3.80 (s, 3 H) 4.13 - 4.19 (m, 1 H) 4.28 - 4.45 (m, 2 H) 4.50 (d, J=7.31 Hz, 1 H) 4.61 - 4.72 (m, 2 H) 4.98 (d, J=4.35 Hz, 1 H) 6.85 (d, J=8.08 Hz, 1 H) 6.92 (t, J=7.54 Hz, 1 H) 7.15 - 7.23 (m, 1 H) 7.37 (d, J=7.31 Hz, 1 H)
135	Et		H	980.7
136	Et		H	994.7	(300 MHz) : 0.83 (d, J=7.15 Hz, 6 H) 0.90 (t, J=7.31 Hz, 3 H) 0.97 (t, J=6.99 Hz, 3 H) 1.04 - 1.35 (m, 18 H) 1.09 (s, 3 H) 1.26 (d, J=6.53 Hz, 3 H) 1.31 (s, 3 H) 1.35 - 1.93 (m, 7 H) 2.12 - 2.67 (m, 12 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.94 (m, 2 H) 3.18 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.58 - 3.67 (m, 1 H) 3.70 (d, J=7.77 Hz, 1 H) 3.81 (s, 3 H) 4.17 (d, J=4.51 Hz, 1 H) 4.24 - 4.33 (m, 1 H) 4.36 - 4.47 (m, 1 H) 4.50 (d, J=7.15 Hz, 1 H) 4.62 - 4.72 (m, 2 H) 4.99 (d, J=4.66 Hz, 1 H) 6.85 (d, J=8.08 Hz, 1 H) 6.92 (t, J=7.38 Hz, 1 H) 7.18 (td, J=7.69, 1.40 Hz, 1 H) 7.40 (d, J=6.68 Hz, 1 H)

[0596] 

[Table 3-3]

137	Et		H		(300 MHz) : 0.79 - 0.86 (m, 6 H) 0.90 (t, J=7.31 Hz, 3 H) 1.06 - 1.28 (m, 2 H) 1.06 - 1.21 (m, 15 H) 1.28 - 1.34 (m, 3 H) 1.45 - 1.95 (m, 5 H) 2.07 - 2.65 (m, 6 H) 2.28 - 2.31 (m, 6 H) 2.37 - 2.37 (m, 3 H) 2.68 - 2.77 (m, 2 H) 2.77 - 2.96 (m, 2 H) 3.13 - 3.35 (m, 3 H) 3.23 - 3.25 (m, 3 H) 3.32 - 3.34 (m, 3 H) 3.41 (d, J=8.70 Hz, 1 H) 3.51 - 3.63 (m, 1 H) 3.71 (d, J=7.93 Hz, 1 H) 3.76 (s, 2 H) 3.84 (s, 3 H) 4.14 - 4.23 (m, 1 H) 4.29 - 4.42 (m, 1 H) 4.45 (d, J=6.84 Hz, 1 H) 4.54 (d, J=9.79 Hz, 1 H) 4.65 (s, 1 H) 4.98 (d, J=4.51 Hz, 1 H) 5.39 (t, J=5.28 Hz, 1 H) 6.83 - 6.95 (m, 2 H) 7.15 - 7.30 (m, 2 H)
138	Et		H	939.6	(300 MHz): 0.78 - 0.87 (m, 6 H) 0.91 (t, J=7.07 Hz, 3 H) 1.05 - 1.28 (m, 17 H) 1.31 - 1.33 (m, 3 H) 1.46 - 1.95 (m, 5 H) 2.11 - 2.48 (m, 6 H) 2.17 - 2.22 (m, 3 H) 2.27 - 2.29 (m, 6 H) 2.37 - 2.38 (m, 3 H) 2.56 (t, J=5.67 Hz, 2 H) 2.74 - 2.97 (m, 2 H) 3.14 - 3.50 (m, J=27.04 Hz, 4 H) 3.24 (s, 3 H) 3.33 (s, 3 H) 3.51 - 3.79 (m, 4 H) 3.86 (s, 3 H) 4.19 - 4.26 (m, 1 H) 4.33 - 4.50 (m, 2 H) 4.56 (d, J=9.79 Hz, 1 H) 4.66 (s, 1 H) 4.97 - 5.01 (m, 1 H) 5.55 - 5.64 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.19 - 7.30 (m, 2 H)
139	Et		H	1045.6	(600 MHz) : 0.76 - 0.85 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.03 - 1.22 (m, 2 H) 1.08 - 1.19 (m, 15 H) 1.31 (s, 3 H) 1.49 - 1.67 (m, 3 H) 1.69 - 1.80 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.09 - 2.20 (m, 1 H) 2.20 - 2.31 (m, 2 H) 2.24 - 2.30 (m, 6 H) 2.36 (s, 3 H) 2.39 (d, J=15.13 Hz, 1 H) 2.46 - 2.66 (m, 4 H) 2.77 - 2.85 (m, 1 H) 2.89 (d, J=14.67 Hz, 1 H) 3.16 - 3.42 (m, 4 H) 3.21 - 3.24 (m, 3 H) 3.31 - 3.33 (m, 3 H) 3.56 - 3.68 (m, 1 H) 3.64 (d, J=8.25 Hz, 4 H) 3.73 (d, J=8.25 Hz, 1 H) 3.81 (s, 6 H) 4.22 (s, 1 H) 4.35 - 4.43 (m, 1 H) 4.45 (d, J=7.34 Hz, 1 H) 4.52 (d, J=9.63 Hz, 1 H) 4.64 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.59 (s, 1 H) 6.83 (d, J=8.25 Hz, 2 H) 6.88 (t, J=7.57 Hz, 2 H) 7.19 (t, J=7.79 Hz, 2 H) 7.33 (d, J=6.42 Hz, 2 H)
140	Et		H	981.7	(600 MHz) : 0.78 - 0.85 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.01 (s, 3 H) 1.05 - 1.33 (m, 23 H) 1.46 - 1.94 (m, 7 H) 2.10 - 2.19 (m, 1 H) 2.20 - 2.69 (m, 9 H) 2.25 - 2.29 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.76 - 2.84 (m, 1 H) 2.89 (d, J=15.13 Hz, 1 H) 3.13 - 3.25 (m, 3 H) 3.22 - 3.24 (m, 3 H) 3.30 (s, 3 H) 3.39 (s, 1 H) 3.56 (s, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.81 (s, 3 H) 4.19 (s, 1 H) 4.33 - 4.42 (m, 2 H) 4.44 (d, J=7.34 Hz, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.73 (s, 1 H) 6.86 (d, J=7.79 Hz, 1 H) 6.90 - 6.97 (m, 1 H) 7.17 - 7.24 (m, 1 H) 7.28 - 7.35 (m, 1 H)
141	Et		H	995.7	(600 MHz) : 0.76 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.97 (s, 3 H) 1.06 - 1.23 (m, 2 H) 1.12 (d, J=7.34 Hz, 3 H) 1.13 - 1.18 (m, 15 H) 1.26 (s, 2 H) 1.30 (s, 3 H) 1.42 (s, 2 H) 1.48 - 1.64 (m, 3 H) 1.75 (s, 1 H) 1.83 (s, 1 H) 2.09 - 2.19 (m, 1 H) 2.20 - 2.69 (m, 9 H) 2.26 - 2.28 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.76 - 2.84 (m, 1 H) 2.89 (d, J=15.13 Hz, 1 H) 3.08 - 3.21 (m, 3 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.46 (m, 1 H) 3.48 - 3.57 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 3.80 (s, 3 H) 4.18 - 4.31 (m, 2 H) 4.32 - 4.44 (m, 2 H) 4.53 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.01 (s, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.89 - 6.96 (m, 1 H) 7.14 - 7.22 (m, 1 H) 7.34 - 7.43 (m, 1 H)
142	Et		H		(600 MHz) : 0.80 - 0.85 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.02 - 1.35 (m, 23 H) 1.30 (s, 3 H) 1.49 - 1.89 (m, 7 H) 2.14 - 2.64 (m, 12 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.91 (m, 1 H) 3.18 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.38 - 3.44 (m, 1 H) 3.59 - 3.65 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 3.80 (s, 3 H) 4.14 - 4.18 (m, 1 H) 4.28 - 4.33 (m, 1 H) 4.37 - 4.43 (m, 1 H) 4.49 (d, J=6.88 Hz, 1 H) 4.63 - 4.70 (m, 2 H) 4.97 (d, J=5.04 Hz, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.89 - 6.94 (m, 1 H) 7.16 - 7.21 (m, 1 H) 7.34 - 7.38 (m, 1 H)

[0597] 

[Table 3-4]

143	Et		H	939.6	(600 MHz) : 0.78 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.04 - 1.20 (m, 8 H) 1.07 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.28 (s, 3 H) 1.49 - 1.59 (m, 2 H) 1.63 - 1.68 (m, 1 H) 1.69 - 1.77 (m, 1 H) 1.80 - 1.86 (m, 1 H) 2.11 - 2.46 (m, 5 H) 2.27 (s, 6 H) 2.34 (s, 3 H) 2.51 - 2.57 (m, 1 H) 2.76 - 2.83 (m, 1 H) 2.86 (d, J=14.21 Hz, 1 H) 3.17 (dd, J=10.32, 7.11 Hz, 1 H) 3.21 (s, 3 H) 3.28 (s, 3 H) 3.34 - 3.49 (m, 3 H) 3.52 - 3.64 (m, 3 H) 3.67 (d, J=8.25 Hz, 1 H) 3.95 (s, 3 H) 4.13 - 4.17 (m, 1 H) 4.31 - 4.37 (m, 1 H) 4.42 (d, J=7.34 Hz, 1 H) 4.50 (d, J=9.63 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.95 (d, J=4.59 Hz, 1 H) 5.35 (t, J=5.73 Hz, 1 H) 6.95 (d, J=7.79 Hz, 1 H) 7.01 - 7.08 (m, 1 H) 7.41 - 7.45 (m, 1 H) 8.12 (t, J=5.50 Hz, 1 H) 8.16 (dd, J=8.25, 1.83 Hz, 1 H)
144	Et		H	975.6	(600 MHz) : 0.77 (d, J=6.88 Hz, 6 H) 0.85 (t, J=7.34 Hz, 3 H) 1.04 - 1.25 (m, 8 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 (s, 3 H) 1.17 (d, J=5.96 Hz, 3 H) 1.27 (s, 3 H) 1.47 - 1.52 (m, 1 H) 1.55 (dd, J=15.13, 5.04 Hz, 1 H) 1.65 - 1.75 (m, 2 H) 1.77 - 1.84 (m, 1 H) 2.08 - 2.42 (m, 5 H) 2.25 (s, 6 H) 2.31 (s, 3 H) 2.51 - 2.57 (m, 1 H) 2.74 - 2.80 (m, 1 H) 2.84 (d, J=14.21 Hz, 1 H) 2.91 - 3.00 (m, 2 H) 3.15 (dd, J=10.32, 7.11 Hz, 1 H) 3.19 (s, 3 H) 3.25 - 3.41 (m, 3 H) 3.29 (s, 3 H) 3.52 - 3.57 (m, 1 H) 3.65 (d, J=8.25 Hz, 1 H) 3.93 (s, 3 H) 4.13 - 4.17 (m, 1 H) 4.33 - 4.37 (m, 1 H) 4.40 (d, J=6.88 Hz, 1 H) 4.47 (d, J=9.63 Hz, 1 H) 4.60 (d, 1 H) 4.93 (d, J=5.04 Hz, 1 H) 5.11 - 5.15 (m, 1 H) 5.25 (t, J=5.73 Hz, 1 H) 6.99 (d, J=8.25 Hz, 1 H) 7.02 (td, J=7.57, 0.92 Hz, 1 H) 7.50 (td, J=7.91, 1.61 Hz, 1 H) 7.82 (dd, J=7.79, 1.83 Hz, 1 H)
145	Et		H	954.6	(600 MHz) : 0.77 (d, J=6.42 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.02 - 1.16 (m, 17 H) 1.24 (s, 3 H) 1.46 - 1.55 (m, 2 H) 1.58 - 1.62 (m, 1 H) 1.66 - 1.73 (m, 1 H) 1.76 - 1.83 (m, 1 H) 2.07 - 2.28 (m, 3 H) 2.22 (s, 6 H) 2.30 (s, 3 H) 2.33 (d, J=15.13 Hz, 1 H) 2.36 - 2.44 (m, 1 H) 2.47 - 2.53 (m, 1 H) 2.73 - 2.78 (m, 1 H) 2.80 - 2.85 (m, 1 H) 3.14 (dd, J=10.32, 7.57 Hz, 1 H) 3.17 (s, 3 H) 3.24 (s, 3 H) 3.26 - 3.42 (m, 5 H) 3.49 - 3.54 (m, 1 H) 3.64 (d, J=7.79 Hz, 1 H) 3.78 (s, 3 H) 4.09 - 4.13 (m, 1 H) 4.29 - 4.34 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.46 (d, J=10.09 Hz, 1 H) 4.57 - 4.62 (m, 1 H) 4.91 (d, J=5.04 Hz, 1 H) 5.27 (s, 1 H) 5.34 (t, J=4.81 Hz, 1 H) 6.77 - 6.82 (m, 1 H) 6.87 (td, J=7.57, 1.38 Hz, 1 H) 6.92 (td, J=7.79, 1.38 Hz, 1 H) 7.91 (dd, J=7.79, 1.38 Hz, 1 H)
146	Et		H	925.5	(600 MHz) : 0.76 (d, J=6.88 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.06 (d, J=7.34 Hz, 14 H) 1.06 (d, J=7.34 Hz, 3 H) 1.25 (s, 3 H) 1.45 - 1.64 (m, 3 H) 1.65 - 1.73 (m, 1 H) 1.75 - 1.83 (m, 3 H) 2.07 - 2.12 (m, 1 H) 2.18 - 2.43 (m, 4 H) 2.23 (s, 6 H) 2.31 (s, 3 H) 2.47 - 2.53 (m, 1 H) 2.74 - 2.78 (m, 1 H) 2.84 (d, J=15.13 Hz, 1 H) 3.10 - 3.17 (m, 3 H) 3.17 (s, 3 H) 3.27 (s, 3 H) 3.25 - 3.42 (m, 3 H) 3.45 - 3.51 (m, 1 H) 3.64 (d, J=8.71 Hz, 1 H) 3.78 (s, 3 H) 4.15 - 4.20 (m, 1 H) 4.29 - 4.34 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.50 (d, J=9.63 Hz, 1 H) 4.55 - 4.61 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 6.52 (dd, J=7.79, 1.38 Hz, 1 H) 6.61 (td, J=7.79, 1.38 Hz, 1 H) 6.71 (dd, J=7.79, 1.38 Hz, 1 H) 6.80 (td, J=7.57, 1.38 Hz, 1 H)
147	Et		H	923.6	(300 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.02 (t, J=7.23 Hz, 3 H) 1.06 - 1.27 (m, 17 H) 1.32 (s, 3 H) 1.45 - 1.91 (m, 5 H) 2.11 - 2.62 (m, 10 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.78 - 2.95 (m, 2 H) 3.15 - 3.48 (m, J=35.28 Hz, 4 H) 3.24 (s, 3 H) 3.36 (s, 3 H) 3.58 (d, J=3.57 Hz, 2 H) 3.59 - 3.67 (m, 1 H) 3.73 (d, J=8.24 Hz, 1 H) 4.18 - 4.26 (m, 1 H) 4.36 - 4.44 (m, 1 H) 4.48 (d, J=7.48 Hz, 1 H) 4.52 - 4.58 (m, 1 H) 4.60 - 4.71 (m, 1 H) 4.98 (d, J=3.26 Hz, 1 H) 5.24 - 5.29 (m, 1 H) 7.21 - 7.32 (m, 5 H)

[0598] 

[Table 3-5]

148	Et		H		(600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.04 (t, J=7.11 Hz, 3 H) 1.01 - 1.22 (m, 14 H) 1.12 (s, 3 H) 1.30 (s, 3 H) 1.49 - 1.64 (m, 3 H) 1.69 - 1.78 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.10 - 2.46 (m, 4 H) 2.24 (s, 6 H) 2.35 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.53 - 2.66 (m, 5 H) 2.78 - 2.84 (m, 1 H) 2.89 (d, J=14.67 Hz, 1 H) 3.16 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.36 (s, 3 H) 3.61 - 3.66 (m, 1 H) 3.67 - 3.73 (m, 2 H) 3.76 - 3.80 (m, 1 H) 4.16 - 4.22 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.47 (d, J=6.88 Hz, 1 H) 4.52 (d, J=10.09 Hz, 1 H) 4.61 - 4.67 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.88 (t, J=4.59 Hz, 1 H) 7.14 (dd, J=7.34, 5.04 Hz, 1 H) 7.32 (d, J=7.79 Hz, 1 H) 7.61 (td, J=7.57, 1.83 Hz, 1 H) 8.59 (d, J=4.58 Hz, 1 H)
149	Et		H	922.7 [M-H]	(600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.01 (t, J=7.11 Hz, 3 H) 1.04 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.50 - 1.79 (m, 4 H) 1.80 - 1.87 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.22 - 2.61 (m, 6 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.41 (d, J=15.59 Hz, 1 H) 2.58 (t, J=5.96 Hz, 2 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=14.21 Hz, 1 H) 3.17 - 3.46 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.56 - 3.61 (m, 2 H) 3.66 - 3.71 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.20 - 4.26 (m, 1 H) 4.35 - 4.47 (m, 2 H) 4.54 (d, J=10.09 Hz, 1 H) 4.59 - 4.67 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.18 - 5.21 (m, 1 H) 7.23 (dd, J=7.34, 5.04 Hz, 1 H) 7.62 (d, J=7.79 Hz, 1 H) 8.47 - 8.51 (m, 2 H)
150	Et		H	924.9	(600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.01 (t, J=7.11 Hz, 3 H) 1.03 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.52 - 1.56 (m, 1 H) 1.57 - 1.62 (m, 1 H) 1.62 - 1.68 (m, 1 H) 1.70 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.22 - 2.65 (m, 7 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.41 (d, J=15.59 Hz, 1 H) 2.58 (t, J=5.96 Hz, 2 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=13.78 Hz, 1 H) 3.19 - 3.44 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.54 - 3.61 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.19 - 4.27 (m, 1 H) 4.36 - 4.41 (m, 1 H) 4.44 (d, J=6.88 Hz, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.63 (d, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.22 (br, s., 1 H) 7.23 (d, J=5.50 Hz, 2 H) 8.51 (d, J=5.04 Hz, 2 H)
151	Et		H		(600 MHz) : 0.79 (d, J=6.88 Hz, 6 H) 0.83 - 0.89 (m, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.03 - 1.23 (m, 17 H) 1.24 - 1.29 (m, 3 H) 1.46 - 1.76 (m, 4 H) 1.78 - 1.87 (m, 1 H) 2.09 - 2.44 (m, 5 H) 2.23 (s, 6 H) 2.33 (s, 3 H) 2.48 - 2.62 (m, 5 H) 2.75 - 2.81 (m, 1 H) 2.82 - 2.89 (m, 1 H) 3.14 - 3.42 (m, 3 H) 3.20 (s, 3 H) 3.33 (s, 3 H) 3.54 - 3.62 (m, 1 H) 3.65 - 3.73 (m, 2 H) 3.76 (s, 2 H) 4.16 - 4.22 (m, 1 H) 4.35 - 4.39 (m, 1 H) 4.43 (d, J=6.88 Hz, 1 H) 4.51 (d, J=10.09 Hz, 1 H) 4.61 (br, s., 1 H) 4.94 (d, J=4.58 Hz, 1 H) 5.26 (t, J=4.59 Hz, 1 H) 7.38 - 7.48 (m, 3 H) 7.66 (s, 1 H) 7.72 - 7.83 (m, 3 H)
152	Et		H		(600 MHz) : 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 (t, J=7.11 Hz, 3 H) 1.07 - 1.22 (m, 17 H) 1.30 (s, 3 H) 1.48 - 1.68 (m, 3 H) 1.70 - 1.79 (m, 1 H) 1.81 - 1.88 (m, 1 H) 2.11 - 2.45 (m, 5 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.69 (m, 3 H) 2.65 (t, J=5.96 Hz, 2 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=14.67 Hz, 1 H) 3.17 - 3.45 (m, 4 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.52 - 3.58 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.97 - 4.04 (m, 2 H) 4.18 - 4.25 (m, 1 H) 4.34 - 4.39 (m, 1 H) 4.42 - 4.45 (m, 1 H) 4.50 (d, J=9.63 Hz, 1 H) 4.61 - 4.66 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.12 - 5.15 (m, 1 H) 7.45 - 7.48 (m, 2 H) 7.49 - 7.53 (m, 2 H) 7.76 (d, J=8.25 Hz, 1 H) 7.84 (d, J=7.79 Hz, 1 H) 8.20 (d, J=8.71 Hz, 1 H)

[0599] 

[Table 3-6]

153	Et		H	974.9	(600 MHz) : 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 (t, J=7.11 Hz, 3 H) 1.17 (d, 17 H) 1.30 (s, 3 H) 1.50 - 1.78 (m, 4 H) 1.81 - 1.87 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.20 - 2.46 (m, 3 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.52 - 2.61 (m, 3 H) 2.64 (t, J=5.96 Hz, 2 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=13.76 Hz, 1 H) 3.17 - 3.44 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.54 - 3.59 (m, 1 H) 3.66 - 3.72 (m, 2 H) 3.74 - 3.81 (m, 2 H) 4.21 - 4.26 (m, 1 H) 4.36 - 4.47 (m, 2 H) 4.54 (d, J=10.09 Hz, 1 H) 4.61 - 4.67 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.22 (t, J=4.36 Hz, 1 H) 7.54 (t, J=7.57 Hz, 1 H) 7.68 (t, J=8.25 Hz, 1 H) 7.80 (d, J=7.79 Hz, 1 H) 8.03 (s, 1 H) 8.08 (d, J=8.71 Hz, 1 H) 8.83 (d, J=2.29 Hz, 1 H)
154	Et		H	974.9	(600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 (t, J=7.11 Hz, 3 H) 1.09 - 1.24 (m, 17 H) 1.30 (s, 3 H) 1.50 - 1.62 (m, 3 H) 1.71 - 1.78 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.11 - 2.18 (m, 1 H) 2.22 - 2.45 (m, 3 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.52 - 2.58 (m, 1 H) 2.58 - 2.64 (m, 2 H) 2.68 (t, J=5.50 Hz, 2 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=13.30 Hz, 1 H) 3.17 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.21 - 3.47 (m, 3 H) 3.34 (s, 3 H) 3.52 - 3.57 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.04 (s, 2 H) 4.22 - 4.26 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.43 (d, J=7.34 Hz, 1 H) 4.52 (d, J=10.09 Hz, 1 H) 4.60 - 4.66 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.14 (t, J=4.81 Hz, 1 H) 7.47 (d, J=4.59 Hz, 1 H) 7.56 (t, J=7.11 Hz, 1 H) 7.70 (t, J=7.57 Hz, 1 H) 8.11 (d, J=8.25 Hz, 1 H) 8.13 (d, J=8.25 Hz, 1 H) 8.84 (d, J=4.58 Hz, 1 H)
155	Et		H		(600 MHz) : 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.04 (t, J=7.11 Hz, 3 H) 1.06 - 1.28 (m, 17 H) 1.31 (s, 3 H) 1.50 - 1.69 (m, 3 H) 1.70 - 1.78 (m, 1 H) 1.81 - 1.88 (m, 1 H) 2.13 - 2.20 (m, 1 H) 2.21 - 2.46 (m, 3 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.52 - 2.63 (m, J=5.96, 5.96 Hz, 3 H) 2.58 (t, J=5.96 Hz, 2 H) 2.79 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.23 (s, 3 H) 3.19 - 3.23 (m, 1 H) 3.25 - 3.30 (m, 2 H) 3.34 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.60 - 3.66 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.77 - 3.84 (m, 2 H) 4.17 - 4.21 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.46 - 4.49 (m, 1 H) 4.54 (d, J=10.09 Hz, 1 H) 4.62 - 4.67 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.33 (t, J=4.36 Hz, 1 H) 6.87 (d, J=3.67 Hz, 1 H) 6.93 (dd, J=5.04, 3.21 Hz, 1 H) 7.19 (d, J=5.04 Hz, 1 H)
156	Et		H		(600 MHz) : 0.78 - 0.84 (m, 6 H) 0.89 (t, J=7.11 Hz, 3 H) 0.95 - 1.33 (m, 17 H) 1.04 (t, J=7.11 Hz, 3 H) 1.30 (s, 3 H) 1.50 - 1.88 (m, 5 H) 2.12 - 2.62 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.79 - 2.93 (m, 2 H) 3.11 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.75 (m, 4 H) 4.17 - 4.20 (m, 1 H) 4.34 - 4.57 (m, 3 H) 4.60 - 4.69 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.40 (br. s., 1 H) 6.14 (d, J=3.21 Hz, 1 H) 6.28 - 6.31 (m, 1 H) 7.34 - 7.37 (m, 1 H)
157	H		H		(600 MHz) : 0.80 - 0.86 (m, 6 H) 0.92 (t, J=6.88 Hz, 3 H) 1.06 - 1.27 (m, 14 H) 1.10 (d, J=7.34 Hz, 3 H) 1.29 (d, J=6.88 Hz, 3 H) 1.31 (s, 3 H) 1.48 - 1.56 (m, 1 H) 1.60 (dd, J=15.13, 5.04 Hz, 1 H) 1.82 - 1.93 (m, 1 H) 2.19 - 2.44 (m, 5 H) 2.24 (s, 6 H) 2.32 (s, 3 H) 2.46 - 2.65 (m, 5 H) 2.75 - 2.82 (m, 1 H) 2.82 - 2.90 (m, 1 H) 3.15 - 3.28 (m, 3 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.44 - 3.52 (m, 1 H) 3.56 - 3.67 (m, 1 H) 3.72 (d, J=7.34 Hz, 1 H) 3.81 - 3.89 (m, 1 H) 3.84 (s, 3 H) 4.17 (br. s., 1 H) 4.31 - 4.41 (m, 3 H) 4.45 (d, J=5.96 Hz, 1 H) 4.52 (d, J=9.63 Hz, 1 H) 4.89 (br. s., 1 H) 5.51 (br. s., 1 H) 6.86 (d, J=8.25 Hz, 1 H) 6.90 (t, J=7.34 Hz, 1 H) 7.20 (t, J=7.79 Hz, 1 H) 7.27 (d, J=6.88 Hz, 1 H)

[0600] 

[Table 3-7]

158	H		H		(600 MHz): 0.80 - 0.86 (m, 6 H) 1.08 - 1.28 (m, 5 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 (s, 3 H) 1.17 (d, J=6.42 Hz, 3 H) 1.19 (d, J=5.96 Hz, 3 H) 1.29 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.55 - 1.65 (m, 2 H) 1.82 - 1.95 (m, 1 H) 2.11 (s, 3 H) 2.19 - 2.35 (m, 3 H) 2.25 (s, 6 H) 2.32 (s, 3 H) 2.39 (d, J=14.67 Hz, 1 H) 2.42 - 2.61 (m, 4 H) 2.76 - 2.82 (m, 1 H) 2.82 - 2.92 (m, 1 H) 3.16 - 3.31 (m, 3 H) 3.25 (s, 3 H) 3.32 (s, 3 H) 3.42 - 3.55 (m, 1 H) 3.59 - 3.66 (m, 1 H) 3.72 (d, J=7.34 Hz, 1 H) 3.84 (s, 3 H) 3.84 - 3.90 (m, 1 H) 4.14 - 4.21 (m, 2 H) 4.32 - 4.41 (m, 2 H) 4.46 (d, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.85 - 4.92 (m, 1 H) 5.49 (br. s., 1 H) 6.87 (d, J=7.79 Hz, 1 H) 6.91 (t, J=7.34 Hz, 1 H) 7.20 (t, J=7.11 Hz, 1 H) 7.25 - 7.27 (m, 1 H)
159	Et		H		(600 MHz) : 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 - 1.25 (m, 14 H) 1.12 (d, J=7.34 Hz, 3 H) 1.29 (d, J=6.88 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.69 (m, 3 H) 1.71 - 1.78 (m, 1 H) 1.81 - 1.87 (m, 1 H) 2.08 - 2.57 (m, 6 H) 2.11 (s, 3 H) 2.24 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.87 - 2.92 (m, 1 H) 3.16 - 3.35 (m, 4 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.46 (m, 2 H) 3.55 - 3.60 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.84 (s, 3 H) 4.14 - 4.24 (m, 2 H) 4.37 - 4.42 (m, 1 H) 4.44 (d, J=6.88 Hz, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.54 (br. s., 1 H) 6.87 (d, J=8.25 Hz, 1 H) 6.91 (t, J=7.34 Hz, 1 H) 7.18 - 7.22 (m, 1 H) 7.26 (dd, J=7.57, 1.60 Hz, 1 H)
160	Me		H	939.9	(600 MHz): 0.79 - 0.88 (m, 6 H) 1.09 - 1.13 (m, 3 H) 1.13 - 1.20 (m, 12 H) 1.20 - 1.33 (m, 2 H) 1.20 - 1.26 (m, 3 H) 1.26 - 1.32 (m, 6 H) 1.56 - 1.63 (m, 1 H) 1.64 - 1.80 (m, 1 H) 1.81 - 1.93 (m, 1 H) 2.05 - 2.31 (m, 3 H) 2.10 - 2.12 (m, 3 H) 2.24 - 2.26 (m, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.43 - 2.59 (m, 4 H) 2.71 - 2.79 (m, 1 H) 2.81 - 2.93 (m, 1 H) 3.17 - 3.30 (m, 3 H) 3.24 - 3.25 (m, 3 H) 3.32 (s, 3 H) 3.34 - 3.48 (m, 1 H) 3.56 - 3.65 (m, 1 H) 3.72 (d, J=8.25 Hz, 1 H) 3.84 (s, 3 H) 4.11 - 4.24 (m, 2 H) 4.34 - 4.42 (m, 1 H) 4.46 (d, J=6.42 Hz, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.84 (s, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 5.50 (s, 1 H) 6.87 (d, J=8.25 Hz, 1 H) 6.91 (t, J=7.34 Hz, 1 H) 7.20 (t, J=7.79 Hz, 1 H) 7.24 - 7.28 (m, 1 H)

[0601] 

[Table 3-8]

161	Me		H	953.9	(600 MHz) : 0.80 - 0.88 (m, 6 H) 0.93 (t, J=6.88 Hz, 3 H) 1.11 (d, J=7.34 Hz, 3 H) 1.13 (s, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.16 - 1.20 (m, 6 H) 1.18 - 1.27 (m, 2 H) 1.20 - 1.24 (m, 3 H) 1.26 - 1.33 (m, 6 H) 1.49 - 1.56 (m, 1 H) 1.60 (dd, J=15.13, 4.59 Hz, 1 H) 1.87 (s, 1 H) 2.09 - 2.18 (m, 1 H) 2.19 - 2.31 (m, 2 H) 2.24 - 2.26 (m, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.44 - 2.66 (m, 6 H) 2.71 - 2.79 (m, 1 H) 2.82 - 2.93 (m, 1 H) 3.16 - 3.23 (m, 3 H) 3.23 - 3.26 (m, 3 H) 3.32 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.55 - 3.64 (m, 1 H) 3.72 (d, J=7.79 Hz, 1 H) 3.84 (s, 3 H) 4.17 (s, 1 H) 4.32 - 4.42 (m, 2 H) 4.46 (d, J=7.34 Hz, 1 H) 4.52 (d, J=9.63 Hz, 1 H) 4.85 (s, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 5.53 (s, 1 H) 6.86 (d, J=8.25 Hz, 1 H) 6.91 (t, J=7.11 Hz, 1 H) 7.20 (t, J=8.48 Hz, 1 H) 7.28 (d, J=6.88 Hz, 1 H)
162	Et		H	939.7	mixture of diastereomers, (600 MHz) : 0.77 - 0.85 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.01 (t, J=7.11 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.42 (d, J=6.88 Hz, 3 H) 1.48 - 1.58 (m, 2 H) 1.60 (dd, J=15.36, 4.81 Hz, 1 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.08 - 2.60 (m, 8 H) 2.23 - 2.26 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.60 - 2.71 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.15 - 3.26 (m, 1 H) 3.22 - 3.23 (m, 3 H) 3.31 - 3.46 (m, 3 H) 3.35 (s, 3 H) 3.56 - 3.67 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 4.11 (s, 1 H) 4.20 (s, 1 H) 4.38 (s, 1 H) 4.48 (s, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.55 (s, 1 H) 8.42 (d, J=2.29 Hz, 1 H) 8.50 - 8.65 (m, 2 H), and (600 MHz) : 0.77 - 0.85 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 (t, J=7.11 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.42 (d, J=6.88 Hz, 3 H) 1.48 - 1.58 (m, 2 H) 1.60 (dd, J=15.36, 4.81 Hz, 1 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.08 - 2.60 (m, 8 H) 2.23 - 2.26 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.60 - 2.71 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.15 - 3.26 (m, 1 H) 3.22 - 3.23 (m, 3 H) 3.31 - 3.46 (m, 3 H) 3.35 (s, 3 H) 3.56 - 3.67 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 4.03 - 4.09 (m, 1 H) 4.20 (s, 1 H) 4.38 (s, 1 H) 4.48 (s, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.44 (s, 1 H) 8.42 (d, J=2.29 Hz, 1 H) 8.50 - 8.65 (m, 2 H)
163	Et		H	969.6	(500 MHz) : 0.78 - 0.85 (m, 6 H) 0.85 - 0.93 (m, 6 H) 1.06 - 1.35 (m, 2 H) 1.11 (d, J=7.40 Hz, 3 H) 1.13 - 1.20 (m, 12 H) 1.29 (s, 3 H) 1.32 (d, J=6.86 Hz, 3 H) 1.48 - 1.65 (m, 3 H) 1.73 (s, 1 H) 1.84 (s, 1 H) 2.09 - 2.46 (m, 5 H) 2.22 - 2.23 (m, 6 H) 2.35 - 2.36 (m, 3 H) 2.47 - 2.70 (m, 5 H) 2.76 - 2.84 (m, 1 H) 2.88 (d, J=13.44 Hz, 1 H) 3.14 - 3.35 (m, 3 H) 3.22 - 3.23 (m, 3 H) 3.33 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.59 - 3.68 (m, 1 H) 3.71 (d, J=7.95 Hz, 1 H) 4.00 (s, 3 H) 4.16 (s, 1 H) 4.33 - 4.43 (m, 2 H) 4.47 (d, J=7.13 Hz, 1 H) 4.53 (d, J=9.60 Hz, 1 H) 4.64 (s, 1 H) 4.96 (d, J=4.66 Hz, 1 H) 6.00 (t, J=4.80 Hz, 1 H) 7.96 (d, J=2.47 Hz, 1 H) 8.14 (d, J=2.74 Hz, 1 H)
164	Et		H	969.8	(500 MHz) : 0.76 - 0.84 (m, 6 H) 0.85 - 0.93 (m, 6 H) 1.05 - 1.20 (m, 2 H) 1.10 (d, J=7.13 Hz, 3H) 1.11 - 1.19 (m, 12 H) 1.29 (s, 3 H) 1.33 (d, J=6.86 Hz, 3 H) 1.45 (d, J=11.52 Hz, 1 H) 1.48 - 1.56 (m, 1 H) 1.59 (dd, J=15.08, 4.94 Hz, 1 H) 1.68 - 1.78 (m, 1 H) 1.78 - 1.87 (m, 1 H) 2.18 - 2.31 (m, 3 H) 2.22 - 2.23 (m, 6 H) 2.35 (s, 3 H) 2.35 - 2.76 (m, 7 H) 2.76 - 2.83 (m, 1 H) 2.88 (d, J=13.99 Hz, 1 H) 3.12 - 3.33 (m, 3 H) 3.21 - 3.22 (m, 3 H) 3.30 - 3.31 (m, 3 H) 3.33 - 3.44 (m, 1 H) 3.48 - 3.57 (m, 1 H) 3.69 (d, J=7.95 Hz, 1 H) 3.99 (s, 3 H) 4.18 (s, 1 H) 4.31 - 4.40 (m, 2 H) 4.42 (d, J=7.13 Hz, 1 H) 4.52 (d, J=9.87 Hz, 1 H) 4.63 (s, 1 H) 4.95 (d, J=4.94 Hz, 1 H) 5.81 (t, J=4.94 Hz, 1 H) 7.96 (d, J=2.74 Hz, 1 H) 8.08 (d, J=2.74 Hz, 1 H)

[0602] 

[Table 3-9]

165	Et		H	938.7	mixture of diastereomers, (600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=6,19 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.35 - 1.38 (m, 3 H) 1.50 - 1.68 (m, 3 H) 1.71 - 1.78 (m, 1 H) 1.81 - 1.87 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.21 - 2.51 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.52 - 2.65 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=12.84 Hz, 1 H) 3.18 - 3.25 (m, 2 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.48 (m, 2 H) 3.54 - 3.60 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.87 - 3.94 (m, 1 H) 4.21 - 4.25 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.12 - 5.17 (m, 1 H) 7.23 (dd, J=7.57, 4.81 Hz, 1 H) 7.63 (dd, J=7.79, 1.83 Hz, 1 H) 8.48 (d, J=4.58 Hz, 1 H) 8.53 (s, 1 H), and (600 MHz) : 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.98 (t, J=6.19 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.35 - 1.38 (m, 3 H) 1.50 - 1.68 (m, 3 H) 1.71 - 1.78 (m, 1 H) 1.81 - 1.87 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.21 - 2.51 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.40 (d, J=15.13 Hz, 1 H) 2.52 - 2.65 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=12.84 Hz, 1 H) 3.18 - 3.25 (m, 2 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.48 (m, 2 H) 3.54 - 3.60 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.87 - 3.94 (m, 1 H) 4.21 - 4.25 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.12 - 5.17 (m, 1 H) 7.23 (dd, J=7.57, 4.81 Hz, 1 H) 7.63 (dd, J=7.79, 1.83 Hz, 1 H) 8.48 (d, J=4.58 Hz, 1 H) 8.53 (s, 1 H)
166	Et		H	968.8	mixture of diastereomers, (600 MHz) : 0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.11 Hz, 3 H) 0.89 - 0.96 (m, 3 H) 1.05 - 1.26 (m, 17 H) 1.29 - 1.32 (m, 3 H) 1.33 - 1.36 (m, 3 H) 1.50 - 1.87 (m, 5 H) 2.14 - 2.18 (m, 1 H) 2.23 - 2.68 (m, 9 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.87 - 2.93 (m, 1 H) 3.18 - 3.49 (m, 4 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.51 - 3.58 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.90 (s, 3 H) 4.20 - 4.25 (m, 1 H) 4.30 - 4.34 (m, 1 H) 4.36 - 4.40 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.46 - 5.51 (m, 1 H) 6.78 (d, J=5.50 Hz, 1 H) 8.38 - 8.41 (m, 2 H), and (600 MHz) : (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.11 Hz, 3 H) 0.89 - 0.96 (m, 3 H) 1.05 - 1.26 (m, 17 H) 1.29 - 1.32 (m, 3 H) 1.33 - 1.36 (m, 3 H) 1.50 - 1.87 (m, 5 H) 2.14 - 2.18 (m, 1 H) 2.23 - 2.68 (m, 9 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.87 - 2.93 (m, 1 H) 3.18 - 3.49 (m, 4 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.51 - 3.58 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.90 (s, 3 H) 4.20 - 4.25 (m, 1 H) 4.30 - 4.34 (m, 1 H) 4.36 - 4.40 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.46 - 5.51 (m, 1 H) 6.78 (d, J=5.50 Hz, 1 H) 8.38 - 8.41 (m, 2 H)

[0603] 

[Table 3-10]

167	Et	OH	Me	733.6	(600 MHz) : 0.75 - 0.81 (m, 6 H) 0.86 (t, J=7.34 Hz, 3 H) 1.03 (s, 3 H) 1.07 (d, J=7.34 Hz, 3 H) 1.08 - 1.23 (m, 8 H) 1.11 (s, 3 H) 1.17 (d, J=5.96 Hz, 3 H) 1.28 (s, 3 H) 1.44 - 1.68 (m, 3 H) 1.71 (dd, J=15.36, 5.27 Hz, 1 H) 1.77 - 1.85 (m, 1 H) 2.05 (d, J=15.59 Hz, 1 H) 2.09 - 2.16 (m, 1 H) 2.15 - 2.25 (m, 2 H) 2.26 (s, 6 H) 2.32 (s, 3 H) 2.36 - 2.43 (m, 1 H) 2.43 - 2.52 (m, 1 H) 2.73 - 2.80 (m, 1 H) 2.81 - 2.88 (m, 1 H) 3.14 - 3.20 (m, 1 H) 3.20 (s, 3 H) 3.25 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.42 - 3.49 (m, 1 H) 3.64 (d, J=7.79 Hz, 1 H) 4.12 - 4.18 (m, 1 H) 4.37 (d, J=7.34 Hz, 1 H) 4.47 (q, J=6.42 Hz, 1 H) 4.58 - 4.64 (m, 1 H) 4.93 (d, J=5.04 Hz, 1 H)
168	Et		OH		(600 MHz) : 0.78 - 0.83 (m, 6 H) 0.87 - 0.94 (m, 3 H) 0.96 - 1.34 (m, 28 H) 1.36 - 1.70 (m, 7 H) 1.80 - 1.91 (m, 2 H) 2.02 (d, J=15.13 Hz, 1 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.29 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.40 - 2.68 (m, 5 H) 2.73 - 2.81 (m, 1 H) 2.83 - 2.91 (m, 1 H) 2.94 - 3.02 (m, 1 H) 3.18 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.32 - 3.38 (m, 1 H) 3.47 - 3.56 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.81 (s, 3 H) 4.16 - 4.34 (m, 2 H) 4.37 (d, J=7.34 Hz, 1 H) 4.39 - 4.47 (m, 1 H) 4.56 - 4.67 (m, 1 H) 4.96 (d, J=4.58 Hz, 1 H) 6.86 (d, J=8.71 Hz, 1 H) 6.94 (t, J=5.96 Hz, 1 H) 7.19 (t, 1 H) 7.44 - 7.49 (m, 1 H)
169	Et		OH	953.7	(600 MHz) : 0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, 3 H) 0.92 (t, J=7.11 Hz, 3 H) 0.95 - 0.99 (m, 3 H) 1.03 - 1.24 (m, 14 H) 1.25 (d, J=6.88 Hz, 3 H) 1.29 (s, 3 H) 1.35 - 1.83 (m, 8 H) 1.88 (dd, J=15.13, 5.04 Hz, 1 H) 2.02 (d, J=14.67 Hz, 1 H) 2.10 - 2.27 (m, 3 H) 2.25 (s, 6 H) 2.34 (s, 3 H) 2.36 - 2.65 (m, 6 H) 2.71 - 2.80 (m, 1 H) 2.88 (d, J=14.67 Hz, 1 H) 3.13 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.25 (s, 3 H) 3.33 - 3.48 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 3.78 (s, 3 H) 4.13 - 4.44 (m, 4 H) 4.54 - 4.65 (m, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 6.82 (d, J=8.25 Hz, 1 H) 6.90 (t, J=7.57 Hz, 1 H) 7.17 (t, J=7.79 Hz, 1 H) 7.29 (d, J=7.79 Hz, 1 H)
170	Et		OH	981.9 FAB MASS	(600 MHz) : 0.81 (d, J=6.88 Hz, 3 H) 0.84 - 0.93 (m, 6 H) 0.97 (t, J=6.65 Hz, 3 H) 1.04 - 1.33 (m, 12 H) 1.09 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.24 (s, 3 H) 1.31 (s, 3 H) 1.34 - 1.83 (m, 8 H) 1.86 (dd, J=14.90, 5.27 Hz, 1 H) 2.03 (d, J=14.67 Hz, 1 H) 2.10 - 2.21 (m, 1 H) 2.23 - 2.29 (m, 2 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.56 (m, 5 H) 2.59 - 2.67 (m, 1 H) 2.73 - 2.81 (m, 1 H) 2.89 (d, J=11.46 Hz, 1 H) 3.17 - 3.23 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.51 - 3.57 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.80 (s, 3 H) 4.13 - 4.40 (m, 2 H) 4.25 - 4.31 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.58 - 4.69 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 6.84 (d, J=7.79 Hz, 1 H) 6.92 (t, J=7.57 Hz, 1 H) 7.18 (t, J=7.11 Hz, 1 H) 7.39 (d, J=5.96 Hz, 1 H)
171	Et		OH	995.9 FAB MASS	(600 MHz): 0.77 - 0.90 (m, 9 H)0.93 - 1.36 (m, 23 H) 1.31 (s, 3 H) 1.36 - 1.88 (m, 7 H) 2.05 - 2.17 (m, 2 H) 2.25 (s, 6 H) 2.23 - 2.54 (m, 8 H) 2.37 (s, 3 H) 2.58 - 2.66 (m, 1 H) 2.69 - 2.75 (m, 1 H) 2.79 - 2.91 (m, 2 H) 3.13 - 3.21 (m, 1 H) 3.20 (s, 3 H) 3.30 (s, 1 H) 3.30 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.55 (dd, J=14.44, 6.19 Hz, 1 H) 3.67 (d, J=8.71 Hz, 1 H) 3.76 - 3.82 (m, 1 H) 3.80 (s, 3 H) 4.29 - 4.37 (m, 3 H) 4.55 - 4.65 (m, 2 H) 4.98 (d, J=4.59 Hz, 1 H) 6.51 (br s, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.92 (t, J=7.57 Hz, 1 H) 7.18 (t, J=7.34 Hz, 1 H) 7.33 - 7.41 (m, 1 H)

Example 126

[0604] 

(1) The compound obtained in Example 7, (3) (5.78 g) was dissolved in ethanol (75 ml), the solution was added with ice-cooled 1 N hydrochloric acid (30 ml), and the mixture was stirred for 30 minutes. The reaction mixture was neutralized with 10% aqueous sodium hydroxide, and then added with ethyl acetate, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 20:1 to 10:1) to obtain a 4"-hydroxy compound (3.97 g).

[0605] 

(2) The compound obtained in (1) mentioned above (3.00 g) was dissolved in tetrahydrofuran (20 ml) and dimethylformamide (10 ml), the solution was added with N,N'-carbonyldiimidazole (1.54 g) and added with sodium hydride (228 mg) under ice cooling, and the mixture was stirred for 1 hour. The mixture was successively added with distilled water, ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was successively washed 3 times with distilled water, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain a 4"-O-imidazolylcarbonyl compound (3.11 g).

[0606] 

(3) The compound obtained in (2) mentioned above (530 mg) was dissolved in tetrahydrofuran (3 ml), and the solution was added with the compound obtained in Reference Example 54 (170 mg). Then, the reaction mixture was concentrated to about 1 ml under reduced pressure. The reaction mixture was left for 2 days, and then concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain a carbamate compound (621 mg).

[0607] 

(4) By using the compound obtained in (3) mentioned above (621 mg) as a starting material, the compound shown in Table 3 (393 mg) was obtained in the same manner as that of Example 7, (4).

Example 127

[0608] By using the compound obtained in Example 126 (1) (0.28 g) as a starting material, the compound shown in Table 3 (0.18 g) was obtained in the same manners as those of Example 113, (2) and Example 7, (4).

Example 128

[0609] The compound obtained in Example 127 (0.17 g) was dissolved in methanol (5 ml), the solution was added with hydroxylamine hydrochloride (49 mg), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with chloroform and 0.1 N aqueous sodium hydroxide. The layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the compound shown in Table 3 (0.177 g).

Example 129

[0610] The compound obtained in Example 128 (0.15 g) was dissolved in ethanol (15 ml), the solution was added with Raney nickel (0.7 g), and the mixture was stirred at room temperature for 31 hours under a hydrogen atmosphere of 3.5 kgt/cm². The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0.1) and preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=9:1:0.1) to obtain the compound shown in Table 3 (2 mg).

Example 130

[0611] 

(1) 6-[2-(2-Carboxyethoxy)ethoxy]-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (84 mg) obtained by the method described in the patent document (WO04/101585) was dissolved in dichloromethane (2 ml), the solution was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (61 mg) under ice cooling, and the mixture was stirred for 30 minutes. The mixture was further added with the compound obtained in Example 126, (1) (100 mg) and 4-dimethylaminopyridine (130 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, and the layers were separated. The organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain a coupling compound (38.9 mg).

(2) By using the compound obtained in (1) mentioned above (38.9 mg) as a starting material, the compound shown in Table 3 (7.1 mg) was obtained in the same manner as that of Example 7, (4).

Example 131

[0612] 

(1) 6-{[2-(2-Carboxyethoxy)ethyl]amino}-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (84 mg) obtained by the method described in the patent document (WO04/101585) was dissolved in dichloromethane (1 ml), the solution was added with triethylamine (19 mg) and pivaloyl chloride (23 mg) under ice cooling, and the mixture was stirred for 30 minutes. The mixture was further added with the compound obtained in Example 126, (1) (100 mg) and 4-dimethylaminopyridine (9.5 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain a coupling compound (97 mg).

(2) By using the compound obtained in (1) mentioned above (97 mg) as a starting material, the compound shown in Table 3 (10.9 mg) was obtained in the same manner as that of Example 7, (4).

Example 132

[0613] 

(1) By using the compound obtained in Example 126, (2) (650 mg) and ethylenediamine (78.1 µl) as starting materials, an amine compound (420 mg) was obtained in the same manner as those of Example 126, (3) and Example 7, (4).

(2) By using the compound obtained in (1) mentioned above (100 mg) and 2-methoxybenzaldehyde (17 mg) as starting materials, an N-benzyl compound (70 mg) was obtained in the same manner as that of Example 7, (2).

(3) By using the compound obtained in (2) mentioned above (10 mg) and acetaldehyde (3.0 µl) as starting materials, the compound shown in Table 3 (5.8 mg) was obtained in the same manner as that of Example 7, (2).

Example 133

[0614] 

(1) The compound obtained in Example 126, (1) (100 mg) was dissolved in toluene (10 ml), the solution was added with triethylamine (200 µl) and 3-chloropropenyl chloride (50 µl), and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:acetone:triethylamine = 50:1:0.1) to obtain a coupling compound (125 mg). By using the resulting coupling compound (125 mg) as a starting material, a 4"-O-vinyl ester compound (78.7 mg) was obtained in the same manner as that of Example 7, (4).

[0615] 

(2) The compound obtained in (1) mentioned above (32 mg) was dissolved in acetonitrile (1 ml), the solution was added with (1S)-1-(2-methoxyphenyl)ethanamine (63 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) and diisopropylethylamine (50 µl), and the mixture was stirred at 100°C for 3 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the compound shown in Table 3 (37 mg).

Example 134

[0616] The compound obtained in Example 133 (37 mg) was dissolved in chloroform (5 ml), and the solution was added with acetaldehyde (11 µl) and sodium triacetoxyborohydride (13 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 3 (2.8 mg).

Example 135

[0617] The compound obtained in Example 126, (1) (50 mg) was dissolved in toluene (1 ml), the solution was added with the compound obtained in Reference Example 55 (30 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (30 mg) and 4-dimethylaminopyridine (65 mg), and the mixture was stirred at 80°C for 5 hours.
The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:acetone:triethylamine = 50:1:0.1) to obtain a coupling compound (11.3 mg).
By using the resulting coupling compound (11.3 mg) as a starting material, the compound shown in Table 3 (2.5 mg) was obtained in the same manner as that of Example 7, (4).

Example 136

[0618] By using the compound obtained in Example 126, (1) (50 mg) and the compound obtained in Reference Example 56 (31 mg) as starting materials, the compound shown in Table 3 (17.8 mg) was obtained in the same manner as that of Example 135.

Example 137

[0619] By using the compound obtained in Example 132, (1) (20 mg) and 2-methoxybenzaldehyde (3.4 mg) as starting materials, the compound shown in Table 3 (10 mg) was obtained in the same manner as that of Example 7, (2).

Example 138

[0620] By using the compound obtained in Example 132, (1) (20 mg) and 2-methoxybenzaldehyde (3.4 mg) as starting materials, and then using 37% aqueous formaldehyde (10.1 mg) as a starting material, the compound shown in Table 3 (5.3 mg) was obtained in the same manner as that of Example 7, (2).

Example 139

[0621] By using the compound obtained in Example 132, (1) (20 mg) and 2-methoxybenzaldehyde (3.4 mg) as starting materials, the compound shown in Table 3 (19.1 mg) was obtained in the same manner as that of Example 7, (2).

Example 140

[0622] By using the compound obtained in Example 126, (2) (20 mg) and the compound obtained in Reference Example 57 (9.1 mg) as starting materials, the compound shown in Table 3 (10.1 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 141

[0623] By using the compound obtained in Example 126, (2) (20 mg) and the compound obtained in Reference Example 58 (9.6 mg) as starting materials, the compound shown in Table 3 (13.9 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 142

[0624] By using the compound obtained in Example 126, (1) (100 mg) and the compound obtained in Reference Example 59 (84 mg) as starting materials, the compound shown in Table 3 (2.6 mg) was obtained in the same manner as that of Example 135.

Example 143

[0625] 

(1) The compound obtained in Example 126, (2) (500 mg) was dissolved in tetrahydrofuran (2 ml), the solution was added with ethylenediamine (64 µl), and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:acetone:triethylamine = 10:1:0.1) to obtain an amine compound (350 mg).

(2) The compound obtained in (1) mentioned above (50 mg) was dissolved in chloroform (1 ml), the solution was added with triethylamine (24 mg) and 2-methoxybenzoyl chloride (12 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography (NH-form) to obtain a coupling compound (56.4 mg). By using the resulting coupling compound (56.4 mg) as a starting material, the compound shown in Table 3 (32.9 mg) was obtained in the same manner as that of Example 7, (4).

Example 144

[0626] By using the compound obtained in Example 143, (1) (50 mg) and 2-methoxybenzenesulfonyl chloride (15 mg) as starting materials, the compound shown in Table 3 (40.2 mg) was obtained in the same manner as that of Example 143, (2).

Example 145

[0627] By using the compound obtained in Example 143, (1) (50 mg) and 2-methoxyphenyl isocyanate (11 mg) as starting materials, the compound shown in Table 3 (36.0 mg) was obtained in the same manner as that of Example 143, (2).

Example 146

[0628] By using the compound obtained in Example 126, (2) (50 mg) and the compound obtained in Reference Example 60 (17.3 mg) as starting materials, the compound shown in Table 3 (21.1 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 147

[0629] By using the compound obtained in Example 126, (2) (667 mg) and the compound obtained in Reference Example 61 (173 mg) as starting materials, the compound shown in Table 3 (463 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 148

[0630] 

(1) The compound obtained in Example 147 (450 mg) was dissolved in methanol (10 ml), the solution was added with 20% palladium hydroxide-carbon (300 mg), and the mixture was stirred at room temperature for 2 days under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure to obtain a debenzylated compound (429 mg).

(2) The compound obtained in (1) mentioned above (30 mg) was dissolved in chloroform, the solution was added with 2-pyridinecarboxaldehyde (19 mg) and sodium triacetoxyborohydride (30 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the compound shown in Table 3 (20.4 mg).

Example 149

[0631] By using the compound obtained in Example 148, (1) (30 mg) and 3-pyridinecarboxaldehyde as starting materials, the compound shown in Table 3 (12.9 mg) was obtained in the same manner as that of Example 148, (2).

Example 150

[0632] By using the compound obtained in Example 148, (1) (30 mg) and 4-pyridinecarboxaldehyde as starting materials, the compound shown in Table 3 (19.8 mg) was obtained in the same manner as that of Example 148, (2).

Example 151

[0633] By using the compound obtained in Example 148, (1) (30 mg) and 2-naphthaldehyde as starting materials, the compound shown in Table 3 (4.5 mg) was obtained in the same manner as that of Example 148, (2).

Example 152

[0634] By using the compound obtained in Example 148, (1) (30 mg) and 1-naphthaldehyde as starting materials, the compound shown in Table 3 (4.0 mg) was obtained in the same manner as that of Example 148, (2).

Example 153

[0635] By using the compound obtained in Example 148, (1) (30 mg) and 3-quinolinecarboxaldehyde as starting materials, the compound shown in Table 3 (10.7 mg) was obtained in the same manner as that of Example 148, (2).

Example 154

[0636] By using the compound obtained in Example 148, (1) (30 mg) and 4-quinolinecarboxaldehyde as starting materials, the compound shown in Table 3 (22.5 mg) was obtained in the same manner as that of Example 148, (2).

Example 155

[0637] By using the compound obtained in Example 148, (1) (30 mg) and 2-thiophenecarboxaldehyde as starting materials, the compound shown in Table 3 (2.8 mg) was obtained in the same manner as that of Example 148, (2).

Example 156

[0638] By using the compound obtained in Example 148, (1) (30 mg) and furfural as starting materials, the compound shown in Table 3 (10.1 mg) was obtained in the same manner as that of Example 148, (2).

Example 157

[0639] 

(1) By using the compound obtained in Example 8, (1) (1.39 g) as a starting material, a cyclized compound (708 mg) was obtained in the same manners as those of Example 7, (2) and (3).

(2) By using the compound obtained in (1) mentioned above (700 mg) as a starting material, 4"-O-imidazolylcarbonyl compound (329 mg) was obtained in the same manners as those of Example 126, (1) and (2).

(3) By using the compound obtained in (2) mentioned above (50 mg) and the compound obtained in Reference Example 54 as starting materials, the compound shown in Table 3 (21.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 158

[0640] By using the compound obtained in Example 157, (2) (50 mg) and the compound obtained in Reference Example 62 as starting materials, the compound shown in Table 3 (24.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 159

[0641] By using the compound obtained in Example 126, (2) (50 mg) and the compound obtained in Reference Example 62 (15 mg) as starting materials, the compound shown in Table 3 (39.2 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 160

[0642] 

(1) By using the compound obtained in Example 1 (1.14 g) and (R)-(+)-propylene oxide (0.2 g) as starting materials, a cyclized compound (189 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (60 mg) as starting materials, a 4"-O-imidazolylcarbonyl compound (40.5 mg) was obtained in the same manners as those of Example 126, (1) and (2).

(3) By using the compound obtained in (2) mentioned above (20 mg) and the compound obtained in Reference Example 62 (6.1 mg) as starting materials, the compound shown in Table 3 (11.1 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 161

[0643] By using the compound obtained in Example 160, (2) (20 mg) and the compound obtained in Reference Example 54 (6.5 mg) as starting materials, the compound shown in Table 3 (10.5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 162

[0644] By using the compound obtained in Example 126, (2) (40 mg) and the compound obtained in Reference Example 63 (19.1 mg) as starting materials, the compound shown in Table 3 (29 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 163

[0645] By using the compound obtained in Example 126, (2) (90.6 mg) and the compound obtained in Reference Example 64 (50 mg) as starting materials, the compound shown in Table 3 (21 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 164

[0646] By using the compound obtained in Example 126, (2) (90.6 mg) and the compound obtained in Reference Example 64 (50 mg) as starting materials, the compound shown in Table 3 (35 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 165

[0647] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 65 (37 mg) as starting materials, the compound shown in Table 3 (32.1 mg) as a mixture of diastereomers was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 166

[0648] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 66 (43 mg) as starting materials, the compound shown in Table 3 (46.8 mg) as a mixture of diastereomers was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 167

[0649] 

(1) The compound obtained in Example 126, (1) (1.79 g) was dissolved in chloroform (purity: 99.5% or higher, 19 ml), the solution was successively added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.09 g), dimethyl sulfoxide (1.34 ml) and pyridinium trifluoroacetate (1.09 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1 to 30:1:0.1) to obtain a 4"-ketone compound (1.52 g).

[0650] 

(2) The compound obtained in (1) mentioned above (15 mg) was dissolved in dichloromethane (3 ml), the solution was added with a 0.84 M solution of methylmagnesium iodide in ether (140 µl) on a dry ice-acetone bath, and the mixture was stirred at the same temperature for 2 hours. The mixture was further stirred at -20°C for 20 minutes. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a 4"-methyl adduct compound (7 mg).

[0651] 

(3) By using the compound obtained in (2) mentioned above (7 mg) as a starting material, the compound shown in Table 3 (5 mg) was obtained in the same manner as that of Example 7, (4).

Example 168

[0652] 

(1) Trimethylsulfoxonium iodide (304 mg) was dissolved in tetrahydrofuran (16 ml), the solution was added with sodium hydride (33 mg) on an ice bath, and the mixture was stirred at the same temperature for 2 hours. Then, the mixture was added with a solution (16 ml) of the compound obtained in Example 167, (1) (0.87 g) in dimethyl sulfoxide, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride, the mixture was extracted with diethyl ether, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1) to obtain an epoxy compound (0.76 g).

[0653] 

(2) The compound obtained in (1) mentioned above (21 mg) was dissolved in ethanol (1 ml), the solution was added with the compound obtained in Reference Example 57 (52 mg) and potassium iodide (37 mg), and the mixture was stirred at 90°C for 20 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated brine and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1 to 30:1:0.1) to obtain an amine compound (35 mg).

[0654] 

(3) By using the compound obtained in (2) mentioned above (35 mg) as a starting material, the compound shown in Table 3 (20 mg) was obtained in the same manner as that of Example 7, (4).

Example 169

[0655] 

(1) By using the compound obtained in Example 168, (1) (73 mg) and the compound obtained in Reference Example 54 as starting materials, an amine compound (40 mg) was obtained in the same manner as that of Example 168, (2).

(2) The compound obtained in (1) mentioned above (40 mg) and ammonium chloride (29 mg) were dissolved in a mixed solvent of methanol-distilled water (2:1, 3 ml), and the solution was stirred at 90°C for 60 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 3 (10 mg).

Example 170

[0656] By using the compound obtained in Example 168, (1) (55 mg) and the compound obtained in Reference Example 58 as starting materials, the compound shown in Table 3 (24 mg) was obtained in the same manners as those of Example 168, (2) and Example 7, (4).

Example 171

[0657] 

(1) The compound obtained in Example 168, (1) (0.43 g) was dissolved in a mixed solvent of methanol-distilled water (2:1, 4.5 ml), the solution was added with sodium azide (0.29 g) and ammonium chloride (0.19 g), and the mixture was stirred at 90°C for 64 hours. The reaction mixture was added with distilled water and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1 to 20:1:0.1) to obtain an azide compound (0.27 g).

[0658] 

(2) The compound obtained in (1) mentioned above (127 mg) was dissolved in tetrahydrofuran (5 ml), the solution was added with a 1 M solution of trimethylphosphine in tetrahydrofuran (1 ml), and the mixture was stirred at room temperature for 5 hours. Then, the mixture was added with distilled water (10 ml), and the mixture was further stirred at room temperature for 60 hours, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain an amine compound (83 mg).

[0659] 

(3) The compound obtained in (2) mentioned above (24 mg) was dissolved in toluene (5 ml), the solution was added with the compound obtained in Reference Example 59 (26 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (19 mg) and 1-hydroxybenzotriazole monohydrate (5 mg), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, then the resulting the residue was added with distilled water and chloroform, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in methanol (100 ml), and the solution was stirred at room temperature for 16 hours and further stirred at 80°C for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 3 (15 mg).

Example 172: Synthesis of the compound represented by the formula (F)

[0660] 

[0661] 

(1) Trimethylsulfonium tetrafluoroborate (73 mg) was dissolved in tetrahydrofuran (4 ml), the solution was slowly added with a 0.5 M solution of potassium bistrimethylsilylamide in toluene (0.8 ml) on a sodium chloride-ice bath under a nitrogen atmosphere, and the mixture was stirred for 2 hours at the same temperature on the ice bath. Then, the mixture was added with a solution of the compound obtained in Example 167, (1) (100 mg) in ethylene glycol dimethyl ether (1 ml) on a dry ice-acetone bath, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:5:0.1) to obtain an epoxy compound (95 mg).

[0662] 

(2) By using the compound obtained in (1) mentioned above (40 mg) as a starting material, the title compound (9 mg) was obtained in the same manners as those of Example 168, (2) and Example 7, (4).
1 H-NMR (600MHz, CDCl₃) δ (ppm): 0.77-0.83 (m, 6H), 0.89 (t, J=7.34Hz, 3H), 0.98 (t, J=6.65Hz, 3H), 1.04-1.38 (m,11H), 1.09 (d, J=10.09Hz, 3H), 1.15 (d, J=7.34Hz, 3H), 1.27 (d, J=6.88Hz, 4H), 1.32 (s, 3H), 1.40-1.66 (m, 5H), 1.68-1.88 (m, 2H), 2.01 (dd, J=15.36, 5.27Hz, 1H), 2.11-2.32 (m, 3H), 2.19 (d, J=15.13Hz, 1H), 2.26 (s, 6H), 2.36 (s, 3H), 2.40-2.66 (m, 5H), 2.75 (d, J=12.84Hz, 1H), 2.81 (m, 1H), 2.91 (d, J=12.84Hz, 1H), 3.16-3.20 (m, 1H), 3.21 (s, 3H), 3.34 (s, 3H), 3.38-3.46 (m, 1H), 3.49-3.56 (m, 1H), 3.67 (d, J=7.79Hz, 1H), 3.77-3.86 (m, 2H), 3.80 (s, 3H), 4.26-4.33 (m, 1H), 4.39-4.49 (m, 3H), 4.60-4.67 (m, 1H), 4.85 (d, J=5.04Hz, 1H), 6.84 (d, J=7.79Hz, 1H), 6.92 (m, 1H), 7.17 (t, J=7.57Hz, 1H), 7.38 (d, J=5.50Hz, 1H)

Example 173: Synthesis of the compound represented by the formula (G)

[0663] 

[0664] 

(1) By using the compound obtained in Example 2 (5.0 g) as a starting material, a cyclized compound (400 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (150 mg) as a starting material, the title compound (36.7 mg) was obtained in the same manners as those of Example 126, (1), (2), (3) and Example 7, (4).
MS (ESI) m/z = 953.7 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.79:1:0.1 (m, 12H), 1.16 (d, 20H), 1.28 (d, J=6.88Hz, 3H), 1.48-1.65 (m, 6H), 2.00-2.10 (m, 1H), 2.14-2.65 (m, 9H), 2.23-2.29 (m, 9H), 2.69-2.80 (m, 1H), 3.15-3.34 (m, 4H), 3.27-3.31 (m, 3H), 3.58-3.73 (m, 2H), 3.83 (s, 3H), 3.84-3.90 (m, 1H), 4.28-4.44 (m, 3H), 4.48-4.56 (m, 2H), 4.80-4.85 (m, 1H), 5.52 (s, 1H), 6.86 (d, J=8.25Hz, 1H), 6.91 (t, J=7.57Hz, 1H), 7.17-7.23 (m, 1H), 7.24-7.30 (m, 1H)

Example 174: Synthesis of the compound represented by the formula (H)

[0665] 

[0666] The compound obtained in Example 126 was dissolved in acetone, the solution was added with acetic anhydride (13.7 mg), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and by using the resulting residue as a starting material, a compound was obtained in the same manner as that of Example 113, (2). The resulting compound was dissolved in methanol, and the solution was stirred under reflux by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the title compound (36.4 mg).
MS (ESI) m/z = 965.5 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.90 (t, J=7.38Hz, 3H), 0.93 (t, J=6.99Hz, 3H), 1.04 (d, J=6.68Hz, 3H), 1.07 (d, J=6.84Hz, 3H), 1.08-1.32 (m, 22H), 1.34-1.68 (m, 5H), 2.02-2.18 (m, 2H), 2.12 (s, 3H), 2.25 (s, 6H), 2.35-2.83 (m, 9H), 3.16-3.35 (m, 4H), 3.25 (s, 3H), 3.31 (s, 3H), 3.57-3.66 (m, 2H), 3.69 (d, J=6.68Hz, 1H), 3.85 (s, 3H), 3.94-3.99 (m, 1H), 4.33-4.42 (m, 2H), 4.46 (d, J=7.15Hz, 1H), 4.53 (d, J=9.79Hz, 1H), 4.93 (d, J=4.35Hz, 1H), 4.94-5.03 (m, 1H), 5.55 (s, 1H), 6.85-6.90 (m, 1H), 6.91-6.95 (m, 1H), 7.18-7.25 (m, 1H), 7.27-7.31 (m, 1H)

Example 175: Synthesis of the compound represented by the formula (I)

[0667] 

[0668] The compound obtained in Example 174 (28 mg) was dissolved in methanol (1 ml), the solution was added with hydroxylamine hydrochloride (10 mg) and imidazole (11.8 mg), and the mixture was stirred for 5 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated aqueous ammonium chloride and chloroform. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol = 10:1 to chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the title compound (24.6 mg).
MS (ESI) m/z = 980.7 [M+H]+
¹H-NMR (300MHz, CDCl₃) δ (ppm): 0.85-0.96 (m, 6H), 1.02-1.29 (m, 22H), 1.26-1.33 (m, 6H), 1.46-1.77 (m, 5H), 1.91-2.09 (m, 2H), 2.07 (s, 3H), 2.23 (s, 6H), 2.33-2.75 (m, 9H), 3.19-3.35 (m, J=5.13Hz, 3H), 3.29 (s, 3H), 3.30 (s, 3H), 3.45-3.88 (m, 4H), 3.82 (s, 3H), 3.93 (d, J=3.57Hz, 1H), 4.29-4.42 (m, 2H), 4.52 (d, J=9.95Hz, 1H), 4.57 (d, J=6.99Hz, 1H), 4.83-4.88 (m, 1H), 4.90 (d, J=4.20Hz, 1H), 5.44 (t, J=4.82Hz, 1H), 6.86 (d, J=8.39Hz, 1H), 6.91 (t, J=7.46Hz, 1H), 7.18-7.31 (m, 2H)

Syntheses of Examples 176 to 205

[0669] Preparation methods of compounds represented by the formula (J) having R^1J, R^2J and R^3J defined in Table 4 are shown below.

[Table 4-1]

[0670] 

Table 4

R1J in the compounds represented by the formula (J) is ethyl group except for the compounds of Examples 177 and 180. R1J in the compound of Example 177 is hydrogen atom, and R1J in the compound of Example 180 is a group represented by the formula:

Example	R2J	R3J	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
176			717.4	(300 MHz) : 0.89 (t, J=7.46 Hz, 3 H) 0.99 - 1.40 (m, 5 H) 1.04 (d, J=6.68 Hz, 3 H) 1.08 (d, J=6.68 Hz, 3 H) 1.12 (d, J=7.46 Hz, 3 H) 1.23 (d, J=6.22 Hz, 3 H) 1.25 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.47 - 1.62 (m, 3 H) 1.62 - 1.70 (m, 1 H) 2.02 - 2.20 (m, 2 H) 2.12 (s, 3 H) 2.29 (s, 6 H) 2.38 (d, J=14.61 Hz, 1 H) 2.42 - 2.57 (m, 2 H) 2.68 - 2.76 (m, 2 H) 2.76 - 2.87 (m, 1 H) 3.01 (d, J=9.33 Hz, 1 H) 3.18 - 3.35 (m, 3 H) 3.25 (s, 3 H) 3.32 (s, 3 H) 3.42 - 3.57 (m, 1 H) 3.62 (q, J=6.68 Hz, 1 H) 3.68 (d, J=7.15 Hz, 1 H) 3.93 (dd, J=8.24, 2.02 Hz, 1 H) 3.98 - 4.10 (m, 1 H) 4.40 (d, J=7.15 Hz, 1 H) 4.91 (d, J=4.51 Hz, 1 H) 4.93 - 5.02 (m, 1 H)

[0671] 

[Table 4-2]

177			689.5	(300 MHz) : 1.06 (d, J=6.68 Hz, 3 H) 1.11 (d, J=7.46 Hz, 3 H) 1.14 (d, J=6.99 Hz, 3 H) 1.18 (d, J=7.15 Hz, 3 H) 1.19 - 1.30 (m, 1 H) 1.22 - 1.24 (m, 3 H) 1.25 (s, 3 H) 1.27 (d, J=6.22 Hz, 3 H) 1.31 (s, 3 H) 1.43 - 1.70 (m, 3 H) 2.02 - 2.25 (m, 3 H) 2.20 (s, 3 H) 2.29 (s, 6 H) 2.38 (d, J=15.23 Hz, 1 H) 2.42 - 2.51 (m, 1 H) 2.64 - 2.88 (m, 3 H) 2.97 - 3.12 (m, 2 H) 3.22 (s, 3 H) 3.24 - 3.30 (m, 1 H) 3.32 (s, 3 H) 3.44 - 3.56 (m, 1 H) 3.69 (d, J=6.84 Hz, 1 H) 3.82 (q, J=6.74 Hz, 1 H) 3.92 (dd, J=6.45, 2.10 Hz, 1 H) 3.97 - 4.09 (m, 2 H) 4.30 - 4.38 (m, 1 H) 4.41 (d, J=7.31 Hz, 1 H) 4.80 (d, J=4.66 Hz, 1 H)
178		H	761.6	(300 MHz) : 0.84 - 0.91 (m, 6 H) 1.02 (d, J=6.53 Hz, 3 H) 1.12 (d, J=7.46 Hz, 3 H) 1.09 - 1.28 (m, 7 H) 1.17 (d, J=6.99 Hz, 3 H) 1.22 (d, J=6.22 Hz, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.37 - 1.88 (m, 6 H) 2.00 - 2.28 (m, 3 H) 2.05 (s, 3 H) 2.17 (s, 3 H) 2.29 (s, 6 H) 2.37 - 2.74 (m, 4 H) 2.90 - 2.98 (m, 1 H) 3.03 (t, J=9.71 Hz, 1 H) 3.26 (s, 3 H) 3.31 - 3.39 (m, 1 H) 3.35 (s, 3 H) 3.50 - 3.59 (m, 1 H) 3.72 (d, J=6.99 Hz, 1 H) 3.98 - 4.12 (m, 2 H) 4.50 (d, J=7.15 Hz, 1 H) 4.73 - 4.79 (m, 1 H) 4.84 - 4.95 (m, 2 H)
179		H	762.6	(300 MHz) : 0.88 (t, J=7.54 Hz, 3 H) 0.95 (d, J=6.84 Hz, 3 H) 1.03 (d, J=6.68 Hz, 3 H) 1.12 (d, J=7.31 Hz, 3 H) 1.10 - 1.28 (m, 7 H) 1.17 (d, J=6.99 Hz, 3 H) 1.22 (d, J=6.06 Hz, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.35 - 1.73 (m, 5 H) 1.99 - 2.27 (m, 4 H) 2.16 (s, 3 H) 2.29 (s, 6 H) 2.37 - 2.74 (m, 5 H) 2.91 - 3.07 (m, 2 H) 3.26 (s, 3 H) 3.32 - 3.58 (m, 2 H) 3.34 (s, 3 H) 3.72 (d, J=6.99 Hz, 1 H) 4.06 (d, 2 H) 4.49 (d, J=7.31 Hz, 1 H) 4.56 (s, 2 H) 4.58 - 4.65 (m, 1 H) 4.87 (d, J=4.66 Hz, 1 H) 4.88 - 4.96 (m, 1 H)
180			916.5	(300 MHz) : 1.02 (d, J=6.68 Hz, 3 H) 1.04 - 1.12 (m, 6 H) 1.14 (d, J=7.31 Hz, 3 H) 1.16 - 1.21 (m, 1 H) 1.22 (d, J=6.06 Hz, 3 H) 1.25 (s, 3 H) 1.30 (d, J=6.22 Hz, 3 H) 1.33 (s, 3 H) 1.35 - 1.42 (m, 1 H) 1.47 - 1.73 (m, 4 H) 1.97 - 2.13 (m, 2 H) 2.06 (s, 3 H) 2.20 (d, J=10.57 Hz, 1 H) 2.28 (s, 6 H) 2.36 (d, J=15.54 Hz, 1 H) 2.39 - 2.58 (m, 2 H) 2.60 - 2.93 (m, 3 H) 3.01 (t, 1 H) 3.06 - 3.26 (m, 2 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.40 - 3.72 (m, 4 H) 3.58 (s, 2 H) 3.86 (d, J=7.31 Hz, 1 H) 4.02 (dd, J=9.25, 5.98 Hz, 1 H) 4.39 (d, J=7.15 Hz, 1 H) 4.86 (d, J=4.35 Hz, 1 H) 4.90 (s, 1 H) 5.93 - 6.04 (m, 1 H) 6.47 (dd, J=3.26, 1.87 Hz, 1 H) 6.68 (d, J=3.42 Hz, 1 H) 7.15 - 7.22 (m, 1 H) 7.35 (t, J=7.69 Hz, 1 H) 7.46 (d, J=1.09 Hz, 1 H) 7.53 - 7.63 (m, 2 H)

[0672] 

[Table 4-3]

181		H	777.7	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.90 (d, J=6.88 Hz, 3 H) 0.99 (d, J=5.96 Hz, 3 H) 1.09 (d, J=7.79 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.17 - 1.30 (m, 2 H) 1.21 (d, J=6.42 Hz, 3 H) 1.23 - 1.24 (m, 6 H) 1.28 (d, J=6.42 Hz, 3 H) 1.48 - 1.67 (m, 4 H) 1.94 - 2.05 (m, 2 H) 2.09 - 2.17 (m, 4 H) 2.17 - 2.25 (m, 1 H) 2.29 (s, 6 H) 2.38 (d, J=15.13 Hz, 1 H) 2.42 - 2.60 (m, 3 H) 2.68 (s, 1 H) 2.93 - 3.05 (m, 2 H) 3.25 (s, 3 H) 3.26 - 3.31 (m, 1 H) 3.32 (s, 3 H) 3.47 - 3.55 (m, 1 H) 3.64 (d, J=7.34 Hz, 1 H) 3.95 - 4.05 (m, 2 H) 4.09 - 4.17 (m, 2 H) 4.48 (d, J=6.88 Hz, 1 H) 4.79 - 4.89 (m, 3 H)
182		H	776.7	(600 MHz) : 0.81 - 0.92 (m, 6 H) 0.99 (s, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.17 - 1.30 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.25 (m, 6 H) 1.27 (d, J=6.42 Hz, 3 H) 1.48 - 1.72 (m, 4 H) 1.94 - 2.06 (m, 2 H) 2.08 - 2.24 (m, 5 H) 2.29 (s, 6 H) 2.39 (d, J=15.59 Hz, 1 H) 2.43 - 2.61 (m, 2 H) 2.68 (s, 1 H) 2.93 - 2.98 (m, 1 H) 2.98 - 3.05 (m, 1 H) 3.23 (s, 3 H) 3.28 - 3.36 (m, 1 H) 3.32 - 3.33 (m, 3 H) 3.41 (s, 2 H) 3.48 - 3.56 (m, 1 H) 3.67 (d, J=6.88 Hz, 1 H) 3.94 - 4.07 (m, 2 H) 4.48 (d, J=5.50 Hz, 1 H) 4.81 (s, 1 H) 4.83 - 4.91 (m, 2 H)
183		H	804.7	(600 MHz) : 0.82 - 0.90 (m, 6 H) 0.98 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.17 - 1.27 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.26 (m, 6 H) 1.29 (d, J=5.96 Hz, 3 H) 1.48 - 1.59 (m, 3 H) 1.59 - 1.65 (m, 1 H) 1.95 - 2.06 (m, 2 H) 2.07 - 2.23 (m, 5 H) 2.27 (s, 6 H) 2.32 (s, 6 H) 2.39 (d, J=15.13 Hz, 1 H) 2.42 - 2.50 (m, 1 H) 2.52 - 2.61 (m, 2 H) 2.68 (s, 1 H) 2.90 - 2.97 (m, 1 H) 3.02 (t, J=9.63 Hz, 1 H) 3.14 (s, 2 H) 3.24 (s, 3 H) 3.28 - 3.38 (m, 1 H) 3.32 - 3.33 (m, 3 H) 3.52 (s, 1 H) 3.68 (d, J=7.34 Hz, 1 H) 3.98 (s, 1 H) 4.01 - 4.08 (m, 1 H) 4.47 (s, 1 H) 4.80 (s, 1 H) 4.83 - 4.93 (m, 2 H)
184		H	949.9	(600 MHz) : 0.82 - 0.89 (m, 6 H) 0.97 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.18 - 1.32 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.26 (m, 3 H) 1.24 - 1.25 (m, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.47 - 1.67 (m, 4 H) 1.90 - 2.07 (m, 2 H) 2.09 - 2.22 (m, 4 H) 2.25 - 2.36 (m, 6 H) 2.38 (d, J=15.59 Hz, 1 H) 2.40 - 2.64 (m, 3 H) 2.65 - 2.74 (m, 1 H) 2.91 (t, J=6.19 Hz, 2 H) 2.92 - 2.98 (m, 1 H) 3.01 (t, J=9.17 Hz, 1 H) 3.22 (s, 3 H) 3.29 - 3.32 (m, 1 H) 3.32 - 3.34 (m, 3 H) 3.40 (d, J=4.13 Hz, 2 H) 3.48 - 3.57 (m, 1 H) 3.67 (d, J=7.34 Hz, 1 H) 3.79 (t, J=6.19 Hz, 2 H) 3.95 - 4.07 (m, 2 H) 4.46 (d, J=8.71 Hz, 1 H) 4.81 (s, 1 H) 4.85 (d, J=5.04 Hz, 1 H) 4.88 (s, 1 H) 7.70 (dd, J=5.50, 3.21 Hz, 2 H) 7.83 (dd, J=5.50, 3.21 Hz, 2 H)

[0673] 

[Table 4-4]

185		H	910.8	(600 MHz) : 0.82 - 0.91 (m, 6 H) 0.97 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 - 1.31 (m, 2 H) 1.20 (d, J=5.96 Hz, 3 H) 1.23 - 1.27 (m, 6 H) 1.29 (d, J=6.42 Hz, 3 H) 1.45 - 1.69 (m, 4 H) 1.93 - 2.09 (m, 2 H) 2.14 - 2.16 (m, 3 H) 2.17 - 2.28 (m, 1 H) 2.29 - 2.31 (m, 6 H) 2.38 (d, J=15.13 Hz, 1 H) 2.41 - 2.61 (m, 3 H) 2.66 - 2.74 (m, 1 H) 2.92 - 3.04 (m, 2 H) 3.21 - 3.34 (m, 1 H) 3.23 - 3.24 (m, 3 H) 3.31 - 3.33 (m, 3 H) 3.46 - 3.55 (m, 1 H) 3.66 (d, J=7.34 Hz, 1 H) 3.87 - 4.07 (m, 4 H) 4.45 (d, J=6.42 Hz, 1 H) 4.81 (s, 1 H) 4.84 - 4.91 (m, 2 H) 5.11 (s, 2 H) 5.27 (s, 1 H) 7.27 - 7.38 (m, 5 H)
186		H	866.8	(600 MHz): 0.81 - 0.91 (m, 6 H) 1.00 (s, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.16 - 1.32 (m, 11 H) 1.20 (d, J=5.96 Hz, 3 H) 1.46 - 1.59 (m, 3 H) 1.60 - 1.67 (m, 1 H) 1.94 - 2.05 (m, 2 H) 2.11 - 2.14 (m, 3 H) 2.15 - 2.24 (m, 1 H) 2.27 - 2.30 (m, 6 H) 2.39 (d, J=15.13 Hz, 1 H) 2.41 - 2.63 (m, 3 H) 2.68 (s, 1 H) 2.92 - 3.04 (m, 2 H) 3.18 (s, 2 H) 3.27 - 3.35 (m, 1 H) 3.32 - 3.33 (m, 3 H) 3.37 (s, 3 H) 3.47 - 3.57 (m, 1 H) 3.67 (d, J=7.34 Hz, 1 H) 3.79 (d, J=1.83 Hz, 2 H) 3.94 - 4.06 (m, 2 H) 4.46 (d, J=5.50 Hz, 1 H) 4.80 - 4.91 (m, 3 H) 7.20 - 7.25 (m, 1 H) 7.27 - 7.33 (m, 4 H)
187		H	880.8	(600 MHz) : 0.80 - 0.90 (m, 6 H) 1.00 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.32 (m, 2 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.22 - 1.31 (m, 9 H) 1.46 - 1.71 (m, 4 H) 1.92 - 2.04 (m, 2 H) 2.06 - 2.24 (m, 4 H) 2.29 - 2.34 (m, 6 H) 2.37 - 2.38 (m, 3 H) 2.38 - 2.42 (m, 1 H) 2.42 - 2.61 (m, 3 H) 2.68 (s, 1 H) 2.92 - 2.98 (m, 1 H) 3.01 (t, J=9.63 Hz, 1 H) 3.16 (s, 3 H) 3.23 (d, J=4.13 Hz, 2 H) 3.30 - 3.36 (m, 1 H) 3.32 - 3.33 (m, 3 H) 3.49 - 3.56 (m, 1 H) 3.66 (d, J=7.34 Hz, 1 H) 3.68 (s, 2 H) 3.94 - 4.06 (m, 2 H) 4.46 (d, J=6.42 Hz, 1 H) 4.79 - 4.91 (m, 3 H) 7.20 - 7.24 (m, 1 H) 7.26 - 7.34 (m, 4 H)
188		H	790.7	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.91 (d, J=6.88 Hz, 3 H) 1.01 (d, J=6.42 Hz, 3 H) 1.07 - 1.11 (m, 6 H) 1.11 - 1.29 (m, 2 H) 1.15 (d, J=6.88 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.22 - 1.30 (m, 9 H) 1.48 - 1.59 (m, 3 H) 1.60 - 1.66 (m, 1 H) 1.97 - 2.09 (m, 2 H) 2.12 - 2.14 (m, 3 H) 2.15 - 2.23 (m, 1 H) 2.28 - 2.29 (m, 6 H) 2.40 (d, J=15.13 Hz, 1 H) 2.45 - 2.58 (m, 3 H) 2.64 - 2.71 (m, 1 H) 2.92 (s, 1 H) 3.01 (t, J=8.94 Hz, 1 H) 3.12 - 3.26 (m, 2 H) 3.22 - 3.22 (m, 3 H) 3.29 - 3.38 (m, 1 H) 3.33 - 3.34 (m, 3 H) 3.49 - 3.56 (m, 1 H) 3.70 (d, J=7.34 Hz, 1 H) 3.98 - 4.10 (m, 2 H) 4.41 - 4.50 (m, 2 H) 4.61 (s, 1 H) 4.81 - 4.96 (m, 2 H)

[0674] 

[Table 4-5]

189		H	868.6	(600 MHz) : 0.87 (t, J=7.57 Hz, 3 H) 0.91 (d, J=6.88 Hz, 3 H) 1.03 (d, J=6.42 Hz, 3 H) 1.04 - 1.32 (m, J=45.85 Hz, 2 H) 1.08 (s, 3 H) 1.16 (d, J=6.88 Hz, 3 H) 1.19 - 1.34 (m, 12 H) 1.46 - 1.62 (m, 4 H) 1.93 - 2.08 (m, 2 H) 2.08 - 2.44 (m, 5 H) 2.13 - 2.17 (m, 9 H) 2.63 - 2.76 (m, 1 H) 2.93 - 3.08 (m, 2 H) 3.14 - 3.26 (m, 5 H) 3.27 - 3.37 (m, 1 H) 3.31 - 3.32 (m, 3 H) 3.38 - 3.49 (m, 2 H) 3.49 - 3.74 (m, 2 H) 3.91 - 4.13 (m, 2 H) 4.47 (d, J=6.42 Hz, 1 H) 4.85 (d, J=4.13 Hz, 1 H) 4.87 - 5.03 (m, 2 H)
190		H	805.7	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.91 (d, J=6.88 Hz, 3 H) 1.01 (d, J=6.42 Hz, 3 H) 1.05 - 1.31 (m, 2 H) 1.10 (d, J=7.79 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.22 - 1.31 (m, 9 H) 1.46 - 1.72 (m, 4 H) 1.96 - 2.10 (m, 2 H) 2.13 - 2.16 (m, 3 H) 2.15 - 2.25 (m, 1 H) 2.28 - 2.31 (m, 6 H) 2.39 (d, J=15.13 Hz, 1 H) 2.44 - 2.59 (m, 3 H) 2.65 - 2.72 (m, 1 H) 2.72 - 2.84 (m, 2 H) 2.93 (s, 1 H) 3.01 (d, J=9.63 Hz, 1 H) 3.12 - 3.28 (m, 2 H) 3.22 - 3.23 (m, 3 H) 3.28 - 3.40 (m, 1 H) 3.32 - 3.34 (m, 3 H) 3.48 - 3.57 (m, 1 H) 3.69 (d, J=6.42 Hz, 1 H) 3.94 - 4.10 (m, 2 H) 4.47 (d, J=6.42 Hz, 1 H) 4.62 (s, 1 H) 4.79 - 5.01 (m, 3 H)
191		H	833.8	(600 MHz) : 0.84 (t, J=7.34 Hz, 3 H) 0.90 (d, J=6.42 Hz, 3 H) 1.00 (d, J=6.88 Hz, 3 H) 1.06 - 1.30 (m, 2 H) 1.08 (d, J=7.34 Hz, 3 H) 1.13 (d, J=6.88 Hz, 3 H) 1.18 (d, J=5.96 Hz, 3 H) 1.20 - 1.23 (m, 6 H) 1.27 (d, J=6.42 Hz, 3 H) 1.46 - 1.58 (m, 3 H) 1.59 - 1.65 (m, 1 H) 1.90 - 2.04 (m, 2 H) 2.04 - 2.20 (m, 12 H) 2.27 - 2.28 (m, 6 H) 2.38 (d, J=15.59 Hz, 1 H) 2.44 - 2.56 (m, 3 H) 2.64 (s, 1 H) 2.90 (s, 1 H) 2.99 (s, 1 H) 3.11 - 3.27 (m, 2 H) 3.20 - 3.21 (m, 3 H) 3.28 - 3.33 (m, 1 H) 3.31 - 3.32 (m, 3 H) 3.48 - 3.56 (m, 1 H) 3.68 - 3.72 (m, 1 H) 3.94 - 4.09 (m, 2 H) 4.43 - 4.50 (m, 1 H) 4.59 - 4.67 (m, 1 H) 4.79 - 4.92 (m, 2 H) 5.03 - 5.09 (m, 1 H)
192		H	939.9	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.89 (d, J=6.42 Hz, 3 H) 0.98 (d, J=6.42 Hz, 3 H) 1.06 - 1.33 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.26 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.46 - 1.69 (m, 4 H) 2.01 - 2.10 (m, 2 H) 2.14 - 2.23 (m, 1 H) 2.15 - 2.16 (m, 3 H) 2.29 - 2.31 (m, 6 H) 2.38 (d, J=15.59 Hz, 1 H) 2.42 - 2.60 (m, 3 H) 2.66 - 2.75 (m, 1 H) 2.93 (s, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.21 - 3.22 (m, 3 H) 3.25 - 3.37 (m, 5 H) 3.31 - 3.32 (m, 3 H) 3.51 (s, 1 H) 3.67 (d, J=7.34 Hz, 1 H) 3.96 - 4.10 (m, 2 H) 4.44 (d, J=7.34 Hz, 1 H) 4.59 (s, 1 H) 4.85 (d, J=4.13 Hz, 1 H) 4.89 - 4.94 (m, 1 H) 4.97 (s, 1 H) 5.08 (s, 2 H) 5.18 (s, 1 H) 7.27 - 7.39 (m, 5 H)

[0675] 

[Table 4-6]

193		H	895.9	(600 MHz) : 0.86 (t, J=7.34 Hz, 3 H) 0.90 (d, J=6.88 Hz, 3 H) 1.00 (d, J=6.42 Hz, 3 H) 1.05 - 1.33 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.16 (d, J=6.88 Hz, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.22 - 1.32 (m, 9 H) 1.46 - 1.74 (m, 4 H) 1.96 - 2.11 (m, 2 H) 2.12 - 2.24 (m, 1 H) 2.14 - 2.17 (m, 3 H) 2.28 - 2.31 (m, 6 H) 2.39 (d, J=15.13 Hz, 1 H) 2.43 - 2.61 (m, 3 H) 2.65 - 2.76 (m, 3 H) 2.93 (s, 1 H) 3.01 (t, J=9.17 Hz, 1 H) 3.18 - 3.38 (m, 3 H) 3.21 - 3.24 (m, 3 H) 3.32 - 3.34 (m, 3 H) 3.47 - 3.58 (m, 1 H) 3.65 - 3.84 (m, 3 H) 3.95 - 4.09 (m, 2 H) 4.46 (d, J=6.88 Hz, 1 H) 4.63 (s, 1 H) 4.80 - 4.94 (m, 2 H) 5.00 (s, 1 H) 7.18 - 7.37 (m, 5 H)
194			731.4	(300 MHz) : 0.88 (t, J=7.54 Hz, 3 H) 0.98 (d, J=6.37 Hz, 3 H) 1.07 (d, J=7.46 Hz, 3 H) 1.08 - 1.84 (m, 8 H) 1.11 - 1.29 (m, 18 H) 1.89 (s, 3 H) 1.99 - 2.12 (m, 1 H) 2.30 (s, 6 H) 2.31 - 2.54 (m, 2 H) 2.55 - 2.78 (m, 3 H) 2.94 - 3.08 (m, 1 H) 3.16 - 3.26 (m, 1 H) 3.33 (s, 3 H) 3.44 (s, 3 H) 3.47 - 3.71 (m, 4 H) 3.86 - 4.12 (m, 2 H) 4.48 (d, J=7.15 Hz, 1 H) 4.82 (d, J=4.35 Hz, 1 H) 4.85 - 4.96 (m, 1 H) 5.36 - 5.80 (m, 2 H)
195		H	718.5	(300 MHz) : 0.80 - 1.00 (m, 9 H) 1.10 - 1.19 (m, 6 H) 1.14 - 1.31 (m, 2 H) 1.21 - 1.25 (m, 3 H) 1.24 (s, 3 H) 1.31 (d, J=6.37 Hz, 3 H) 1.35 (s, 3 H) 1.46 - 1.82 (m, 5 H) 1.89 - 2.57 (m, 5 H) 2.26 - 2.31 (m, 9 H) 2.37 (d, J=14.92 Hz, 1 H) 2.65 - 2.86 (m, 2 H) 3.02 (t, J=9.56 Hz, 1 H) 3.12 - 3.53 (m, 3 H) 3.30 - 3.34 (m, 6 H) 3.74 (d, J=8.39 Hz, 1 H) 3.96 - 4.11 (m, 2 H) 4.38 (d, J=7.31 Hz, 1 H) 4.62 - 4.78 (m, 1 H) 4.81 - 4.94 (m, 1 H)
196		H	796.4	(300 MHz) : 0.84 - 0.91 (m, 3 H) 0.99 (d, J=7.46 Hz, 3 H) 1.04 (d, J=7.15 Hz, 3 H) 1.10 (d, J=7.15 Hz, 3 H) 1.08 - 1.28 (m, 2 H) 1.19 (d, J=6.99 Hz, 3 H) 1.23 (d, J=6.22 Hz, 3 H) 1.25 (s, 3 H) 1.28 - 1.33 (m, 6 H) 1.42 - 1.71 (m, 4 H) 1.89 - 2.01 (m, 1 H) 2.03 - 2.52 (m, 14 H) 2.59 - 2.72 (m, 1 H) 2.76 - 2.93 (m, 2 H) 2.95 (s, 3 H) 3.03 (t, J=9.64 Hz, 1 H) 3.14 - 3.32 (m, 2 H) 3.32 (s, 3 H) 3.34 (s, 3 H) 3.43 - 3.57 (m, 1 H) 3.76 (d, J=8.08 Hz, 1 H) 3.97 - 4.10 (m, 2 H) 4.45 (d, J=6.99 Hz, 1 H) 4.87 - 4.93 (m, 1 H) 5.08 - 5.26 (m, 1 H) 6.04 - 6.21 (m, 1 H)
197		H	761.7
198		H	895.7

[0676] 

[Table 4-7]

199		H	759.5	(600 MHz) : 0.84 (t, J=7.11 Hz, 3 H) 0.93 (d, J=7.34 Hz, 3 H) 1.00 (d, J=6.88 Hz, 3 H) 1.12 (d, J=3.67 Hz, 3 H) 1.14 - 1.28 (m, 2 H) 1.16 (d, J=6.88 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.21 - 1.22 (m, 3 H) 1.24 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.40 - 1.48 (m, 2 H) 1.54 (dd, J=15.13, 5.04 Hz, 1 H) 1.62 - 1.69 (m, 1 H) 2.01 (s, 3 H) 2.11 - 2.32 (m, 15 H) 2.35 (d, J=15.13 Hz, 1 H) 2.44 - 2.54 (m, 1 H) 2.58 - 2.67 (m, 1 H) 2.76 - 2.88 (m, 1 H) 2.99 (d, J=9.17 Hz, 1 H) 3.14 - 3.23 (m, 1 H) 3.25 (s, 3 H) 3.28 (s, 3 H) 3.41 - 3.49 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 3.97 - 4.06 (m, 1 H) 4.07 - 4.16 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.78 - 4.95 (m, 2 H) 7.01 (br. s., 1 H)
200		H	866.9	(600 MHz) : 0.83 (t, J=7.11 Hz, 3 H) 0.94 (d, J=6.42 Hz, 3 H) 1.02 (d, J=6.42 Hz, 3 H) 1.12 (d, J=7.34 Hz, 3 H) 1.16 (d, J=6.88 Hz, 3 H) 1.17 - 1.21 (m, 1 H) 1.20 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.24 - 1.30 (m, 7 H) 1.42 - 1.51 (m, 2 H) 1.54 (dd, J=15.36, 4.81 Hz, 1 H) 1.94 - 2.06 (m, 1 H) 2.07 - 2.50 (m, 16 H) 2.54 - 2.68 (m, 1 H) 2.75 - 2.83 (m, 1 H) 2.88 - 2.96 (m, 1 H) 2.99 (d, J=9.17 Hz, 1 H) 3.17 - 3.35 (m, 2 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.43 - 3.50 (m, 1 H) 3.67 (d, J=8.25 Hz, 1 H) 3.94 (s, 2 H) 3.96 - 4.18 (m, 2 H) 4.40 (d, J=7.34 Hz, 1 H) 4.61 (s, 2 H) 4.83 - 4.91 (m, 2 H) 7.11 (br. s., 1 H) 7.27 - 7.38 (m, 5 H)
201		H	766.8	(600 MHz) : 0.81 - 0.93 (m, 3 H) 0.97 (d, J=7.34 Hz, 3 H) 1.02 - 1.19 (m, 7 H) 1.19 - 1.27 (m, 4 H) 1.21 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.26 (s, 3 H) 1.29 (d, J=5.96 Hz, 3 H) 1.41 - 1.50 (m, 2 H) 1.55 (dd, J=15.13, 4.59 Hz, 1 H) 1.64 (d, J=11.46 Hz, 1 H) 2.08 - 2.40 (m, 4 H) 2.26 - 2.28 (m, 9 H) 2.37 (d, J=15.13 Hz, 1 H) 2.40 - 2.52 (m, 2 H) 2.63 - 2.70 (m, 1 H) 2.80 - 2.88 (m, 1 H) 3.00 (d, J=9.63 Hz, 1 H) 3.19 (dd, J=10.32, 7.11 Hz, 1 H) 3.26 (s, 3 H) 3.29 (s, 3 H) 3.42 - 3.51 (m, 2 H) 3.72 (d, J=8.25 Hz, 1 H) 3.99 - 4.14 (m, 4 H) 4.40 (d, J=6.88 Hz, 1 H) 4.76 - 4.82 (m, 1 H) 4.83 - 4.91 (m, 1 H)
202		H	774.5	(600 MHz) : 0.86 (t, J=7.11 Hz, 3 H) 0.96 - 1.01 (m, 6 H) 1.04 - 1.17 (m, 7 H) 1.17 - 1.26 (m, 4 H) 1.20 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.25 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.42 - 1.52 (m, 2 H) 1.54 (dd, J=15.13, 4.59 Hz, 1 H) 1.67 (d, J=13.30 Hz, 1 H) 1.79 - 1.93 (m, 1 H) 1.93 - 2.25 (m, 2 H) 2.14 - 2.16 (m, 3 H) 2.28 - 2.34 (m, 6 H) 2.37 (d, J=15.13 Hz, 1 H) 2.48 - 2.63 (m, 1 H) 2.72 - 2.85 (m, 2 H) 2.99 (d, J=9.17 Hz, 1 H) 3.15 - 3.26 (m, 1 H) 3.23 (s, 3 H) 3.29 (s, 3 H) 3.33 - 3.40 (m, 2 H) 3.43 - 3.50 (m, 1 H) 3.69 (d, J=8.71 Hz, 1 H) 3.94 - 4.05 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.41 (d, J=7.34 Hz, 1 H) 4.77 - 4.92 (m, 2 H) 7.53 (br. s., 1 H)
203		H	803.7

[0677] 

[Table 4-8]

204		H	789.9	(600 MHz) : 0.83 (t, J=7.34 Hz, 3 H) 0.93 (d, J=7.34 Hz, 3 H) 1.00 (d, J=6.88 Hz, 3 H) 1.04 - 1.14 (m, 7 H) 1.19 (d, J=6.88 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.22 - 1.28 (m, 7 H) 1.30 (d, J=5.96 Hz, 3 H) 1.36 - 1.47 (m, 2 H) 1.56 (dd, J=15.13, 5.04 Hz, 1 H) 1.62 - 1.69 (m, 1 H) 1.74 - 1.88 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.20 - 2.33 (m, 12 H) 2.37 (d, J=15.13 Hz, 1 H) 2.41 - 2.49 (m, 1 H) 2.58 - 2.66 (m, 1 H) 2.80 - 2.91 (m, 2 H) 2.98 - 3.04 (m, 1 H) 3.13 - 3.33 (m, 4 H) 3.26 (s, 3 H) 3.30 (s, 3 H) 3.41 - 3.49 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 3.99 - 4.11 (m, 2 H) 4.38 (d, J=7.34 Hz, 1 H) 4.90 (d, J=4.13 Hz, 1 H) 4.93 - 5.12 (m, 2 H) 5.46 (br. s., 1 H)
205		H	746.8	(600 MHz) : 0.88 (t, J=7.34 Hz, 3 H) 1.04 (d, J=6.42 Hz, 3 H) 1.07 - 1.20 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.25 (m, 7 H) 1.27 (d, J=6.42 Hz, 3 H) 1.33 (s, 3 H) 1.50 - 1.75 (m, J=15.13, 5.04 Hz, 3 H) 1.55 (dd, J=15.13, 5.04 Hz, 1 H) 1.93 - 2.10 (m, 2 H) 2.15 - 2.41 (m, 17 H) 2.38 (d, J=15.13 Hz, 1 H) 2.44 - 2.60 (m, 3 H) 2.62 - 2.69 (m, 1 H) 3.01 (d, J=9.17 Hz, 1 H) 3.19 - 3.30 (m, 1 H) 3.27 (s, 3 H) 3.32 (s, 3 H) 3.46 - 3.55 (m, 1 H) 3.72 (d, J=7.34 Hz, 1 H) 3.98 - 4.09 (m, 2 H) 4.41 - 4.49 (m, 1 H) 4.86 (d, J=4.58 Hz, 1 H) 4.95 - 5.04 (m, 1 H)

Example 176

[0678] 

(1) The compound obtained in Example 126, (1) (1.34 g) was dissolved in chloroform (25 ml), the solution was added with pyridine (2.28 ml) and triphosgene (1.30 g) under ice cooling, and the mixture was stirred for 30 minutes. The mixture was further added with benzyl alcohol (3.05 g), the mixture was stirred for 1 hour, and then added with distilled water, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 650:50:0.1) to obtain a 4"-O-benzyloxycarbonyl compound (1.59 g).

[0679] 

(2) By using the compound obtained in (1) mentioned above (1.59 g) as a starting material, a desilylated compound (1.08 g) was obtained in the same manner as that of Example 7, (4).

[0680] 

(3) The compound obtained in (2) mentioned above (1.08 g) was dissolved in acetone (10 ml), the solution was added with acetic anhydride (155 mg), and the mixture was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The resulting filtrate was concentrated under reduced pressure to obtain a 2'-O-acetyl compound (1.00 g).

[0681] 

(4) N-Chlorosuccinimide (746 mg) was suspended in toluene (30 ml), the mixture was added dropwise with dimethyl sulfide (1.35 ml) at -25°C, and the mixture was stirred at the same temperature for 15 minutes. The mixture was added dropwise with a solution of the compound obtained in (3) mentioned above (500 mg) in toluene (5 ml), and the mixture was stirred at the same temperature for 15 minutes. The mixture was further added with triethylamine (1.56 ml), the mixture was warmed to room temperature 10 minutes later, and then added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 10:10:0.1) to obtain a 9-ketone compound (465 mg).

[0682] 

(5) The compound obtained in (4) mentioned above (460 mg) was dissolved in methanol, the solution was stirred at room temperature for 40 hours. The reaction mixture was added with 5% palladium-carbon (450 mg), and the mixture was stirred at room temperature for 1.5 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 4 (308 mg).

Example 177

[0683] By using the compound obtained in Example 157, (1) (240 mg) as a starting material, the compound shown in Table 4 (31.0 mg) was obtained in the same manners as those of Example 126, (1) and Example 176.

Example 178

[0684] The compound obtained in Example 176, (3) (50 mg) was dissolved in chloroform (0.5 ml) and pyridine (0.5 ml), the solution was added with acetic anhydride (29 mg) and 4-dimethylaminopyridine (14 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1). By using the resulting 9-O-acetyl compound (51.6 mg) as a starting material, the compound shown in Table 4 (31.8 mg) was obtained in the same manner as that of Example 176, (5).

Example 179

[0685] The compound obtained in Example 176, (3) (50 mg) was dissolved in chloroform (1 ml), the solution was added with trichloroacetyl isocyanate (8 µl), and the mixture was stirred for 10 minutes. The reaction mixture was added with methanol (6 µl) and potassium carbonate (9.3 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1), and by using the resulting 9-O-carbamoyl compound (38.6 mg) as a starting material, the compound shown in Table 4 (14.5 mg) was obtained in the same manner as that of Example 176, (5).

Example 180

[0686] By using the compound obtained in Example 23, (2) (0.98 g) as a starting material, the compound shown in Table 4 (207 mg) was obtained in the same manner as that of Example 176.

Example 181

[0687] 

(1) The compound obtained in Example 176, (3) (50 mg) was dissolved in chloroform (2 ml), the solution was added with pyridine (1 ml), benzyl chloroacetate (26.4 µl) and 4-dimethylaminopyridine (13.6 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, and the layers were separated. The organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a 9-O-acyl compound (52.9 mg).

[0688] 

(2) The compound obtained in (1) mentioned above (35 mg) was dissolved in methanol (1 ml), the solution was stirred at room temperature for 18 hours, further stirred at 45°C for 8 hours and stirred at room temperature for 18 hours. The solution was added with 5% palladium-carbon (20 mg), and the mixture was stirred at room temperature for 4 days under a hydrogen atmosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 4 (13.0 mg).

Example 182

[0689] 

(1) The compound obtained in Example 176, (3) (250 mg) was dissolved in chloroform (2 ml), the solution was added with pyridine (5 ml), chloroacetic anhydride (478 mg) and 4-dimethylaminopyridine (160 mg), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform alone) to chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain a 9-O-acyl compound (217 mg).

[0690] 

(2) The compound obtained in (1) mentioned above (215 mg) was dissolved in dimethylformamide (5 ml), the solution was added with sodium azide (21.6 mg), and the mixture was stirred at 80°C for 3.5 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform alone to chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain an azide compound (158 mg).

[0691] 

(3) The compound obtained in (2) mentioned above (155 mg) was dissolved in ethyl acetate (5 ml), the solution was added with 5% palladium-carbon (30 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (5 ml), the solution was added with 5% palladium-carbon (100 mg), and the mixture was stirred at room temperature for 4 hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain an amine compound.

[0692] 

(4) The compound obtained in (3) mentioned above was dissolved in methanol (5 ml), and the solution was stirred at 50°C for 3 hours and stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain the compound shown in Table 4 (78 mg).

Example 183

[0693] By using the compound obtained in Example 182 (20 mg) as a starting material, the compound shown in Table 4 (10.9 mg) was obtained in the same manner as that of Example 7, (2).

Example 184

[0694] The compound obtained in Example 182 (10 mg) was dissolved in chloroform (0.5 ml), the solution was added with phthalimide acetaldehyde (2.9 mg) and sodium triacetoxyborohydride (4.1 mg), and the mixture was stirred at room temperature for 1 hour. The mixture was further added with phthalimide acetaldehyde (12 mg) and sodium triacetoxyborohydride (16 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form, chloroform alone) and preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 4 (2.1 mg).

Example 185

[0695] 

(1) The compound obtained in Example 182, (3) (10 mg) was dissolved in chloroform (0.5 ml), the solution was added with triethylamine (2 µl) and benzyloxychloroformate (2 µl), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an N-benzyloxycarbonyl compound (12.5 mg).

(2) By using the compound obtained in (1) mentioned above (12 mg) as a starting material, the compound shown in Table 4 (4.3 mg) was obtained in the same manner as that of Example 182, (4).

Example 186

[0696] By using the compound obtained in Example 182 (20 mg) and benzaldehyde (3.0 mg) as starting materials, the compound shown in Table 4 (9.3 mg) was obtained in the same manner as that of Example 7, (2).

Example 187

[0697] By using the compound obtained in Example 186 (5.8 mg) as a starting material, the compound shown in Table 4 (2.7 mg) was obtained in the same manner as that of Example 7, (2).

Example 188

[0698] 

(1) The compound obtained in Example 176, (3) (10 mg) was dissolved in toluene (0.1 ml), the solution was added with ethyl isocyanate (44 µl) and 4-dimethylaminopyridine (21.3 mg), and the mixture was stirred at 120°C for 6 hours. The mixture was further added with ethyl isocyanate (88 µl), and the mixture was stirred at 120°C for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 10:10:0.2) to obtain a carbamate compound (10.6 mg).

(2) By using the compound obtained in (1) mentioned above (15 mg) as a starting material, the compound shown in Table 4 (3.5 mg) was obtained in the same manner as that of Example 181, (2).

Example 189

[0699] 

(1) The compound obtained in Example 176, (3) (100 mg) was dissolved in toluene (0.5 ml), the solution was added with 2-bromoethyl isocyanate (101 µl), and the mixture was stirred at 120°C for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 20:1 to hexane:acetone:triethylamine = 10:10:0.2) to obtain a carbamate compound (100 mg).

(2) By using the compound obtained in (1) mentioned above (100 mg) as a starting material, the compound shown in Table 4 (55 mg) was obtained in the same manner as that of Example 181, (2).

Example 190

[0700] 

(1) The compound obtained in Example 189 (20 mg) was dissolved in dimethylformamide (0.5 ml), the solution was added with sodium azide (2.2 mg), and the mixture was stirred at 120°C for 3 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an azide compound (18 mg).

(2) The compound obtained in (1) mentioned above (18 mg) was dissolved in a mixed solvent of methanol-ethyl acetate (1:1, 0.3 ml), the solution was added with 5% palladium-carbon (9 mg), and the mixture was stirred at room temperature for 2.5 hours under hydrogen atmosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 4 (7.9 mg).

Example 191

[0701] By using the compound obtained in Example 190 (15 mg) as a starting material, the compound shown in Table 4 (3.8 mg) was obtained in the same manner as that of Example 7, (2).

Example 192

[0702] By using the compound obtained in Example 190 (15 mg) as a starting material, the compound shown in Table 4 (1.3 mg) was obtained in the same manners as those of Example 185, (1) and Example 182, (4).

Example 193

[0703] By using the compound obtained in Example 190 (30 mg) and benzaldehyde (4.35 mg) as starting materials, the compound shown in Table 4 (4.4 mg) was obtained in the same manner as that of Example 7, (2).

Example 194

[0704] The compound obtained in Example 176 (0.22 g) was dissolved in ethanol (7 ml), the solution was added with hydrazine monohydrate (0.15 ml), and the mixture was stirred for 7 hours under reflux by heating. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in ethanol (7 ml), the solution was added with hydrazine monohydrate (0.15 ml), and the mixture was stirred for 7 hours under reflux by heating. The reaction mixture was added with distilled water and chloroform, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the compound shown in Table 4 (0.19 g).

Example 195

[0705] The compound obtained in Example 194 (190 mg) was dissolved in a mixed solvent of methanol-distilled water (2:1, 4.5 ml), and the solution was added with 3 N hydrochloric acid (150 µl) on a sodium chloride-ice bath. The mixture was slowly added with an aqueous solution (0.6 ml) of sodium nitrite (90 mg). The mixture was further added with 3 N hydrochloric acid (360 µl), and the mixture was adjusted to pH 4, and stirred at the same temperature for 15 minutes. The mixture was successively added with potassium carbonate (201 mg), methanol (1 ml) and sodium borohydride (10 mg), and the mixture was further stirred at the same temperature for 30 minutes. The reaction mixture was adjusted to pH 2 with 3 N hydrochloric acid, and further stirred for 30 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the
organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 4 (110 mg).

Example 196

[0706] The compound obtained in Example 195 (25 mg) was dissolved in diethyl ether (3 ml), the solution was added with methanesulfonyl chloride (50 µl) and an aqueous solution (1 ml) of sodium hydrogencarbonate (15 mg), and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was added with diethyl ether and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=9:1:0.1) to obtain the compound shown in Table 4 (15 mg).

Example 197

[0707] 

(1) By using the compound obtained in Example 195 (58 mg) and phthalimide acetaldehyde as starting materials, a phthalimide compound (38 mg) was obtained in the same manner as that of Example 7, (2).

(2) The compound obtained in (1) mentioned above (38 mg) was dissolved in ethanol (1 ml), the solution was added with hydrazine monohydrate (1 µl), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 5:1:0.1) to obtain the compound shown in Table 4 (5 mg).

Example 198

[0708] 

(1) The compound obtained in Example 197, (1) (16 mg) was dissolved in diethyl ether (3 ml), the solution was added with an aqueous solution (1 ml) of sodium hydrogencarbonate (10 mg) and benzyl chloroformate (6 µl), and the mixture was vigorously stirred for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and diethyl ether, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting residue was dissolved in methanol (10 ml), and the solution was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain a 9-N-benzyloxycarbonyl compound (10 mg).

(2) By using the compound obtained in (1) mentioned above (38 mg) as a starting material, the compound shown in Table 4 (7 mg) was obtained in the same manner as that of Example 197, (2).

Example 199

[0709] By using the compound obtained in Example 195 (20 mg) and acetyl chloride (3 µl) as starting materials, the compound shown in Table 4 (11 mg) was obtained in the same manner as that of Example 198, (1).

Example 200

[0710] By using the compound obtained in Example 195 (30 mg) and benzyl chloroacetate (13 µl) as starting materials, the compound shown in Table 4 (12 mg) was obtained in the same manner as that of Example 198, (1).

Example 201

[0711] By using the compound obtained in Example 200 (15 mg) as a starting material, the compound shown in Table 4 (10 mg) was obtained in the same manner as that of Example 81.

Example 202

[0712] 

(1) By using the compound obtained in Example 195 (58 mg) and chloroacetyl chloride (13 µl) as starting materials, a chloromethyl compound (38 mg) was obtained in the same manner as that of Example 198, (1).

[0713] 

(2) The compound obtained in (1) mentioned above (38 mg) was dissolved in dimethylformamide (1 ml), the solution was added with sodium azide (9 mg), and the mixture was stirred for 4 hours on an oil bath at 120°C. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain an azide compound (21 mg).

[0714] 

(3) The compound obtained in (2) mentioned above (21 mg) was dissolved in a mixed solvent of methanol-ethyl acetate (1:1, 1 ml), the solution was added with 5% palladium-carbon (21 mg), and the mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 4 (14 mg).

Example 203

[0715] By using the compound obtained in Example 202 (8 mg) as a starting material, the compound shown in Table 4 (6 mg) was obtained in the same manner as that of Example 7, (2).

Example 204

[0716] The compound obtained in Example 195 (16 mg) was dissolved in dichloromethane (1 ml), the solution was added with ethyl isocyanate (4 µl), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 4 (9 mg).

Example 205

[0717] By using the compound obtained in Example 195 (10 mg) as a starting material, the compound shown in Table 4 (7 mg) was obtained in the same manner as that of Example 7, (2).

Example 206: Synthesis of the compound represented by the formula (K)

[0718] 

[0719] 

(1) By using the compound obtained in Example 3 as a starting material, a cyclized compound (995 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

[0720] 

(2) The compound obtained in (1) mentioned above (500 mg) was dissolved in methanol (5 ml), the solution was added with 20% palladium hydroxide-carbon (100 mg), and the mixture was stirred at room temperature for 24 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 100:1:0.1) to obtain a debenzylated compound (500 mg).

[0721] 

(3) By using the compound obtained in (2) mentioned above (400 mg) as a starting material, a 9-ketone compound (421 mg) was obtained in the same manner as that of Example 113, (2).

[0722] 

(4) By using the compound obtained in (3) mentioned above (10 mg) as a starting material, the title compound (5 mg) was obtained in the same manner as that of Example 7, (4).
MS (ESI) m/z = 703.5 [M+H]^+
1H-NMR (600MHz, CDCl₃) δ (ppm): 0.90 (t, J=7.57Hz, 3H), 0.93 (d, J=6.42Hz, 3H), 1.01 (d, J=6.88Hz, 3H), 1.07 (d, J=7.34Hz, 3H), 1.11 (d, J=7.34Hz, 3H), 1.21 (d, J=5.96Hz, 3H), 1.22 (s, 3H), 1.23-1.25 (m, 1H), 1.26 (d, J=5.96Hz, 3H), 1.30 (s, 3H), 1.52 (dd, J=15.36, 4.81Hz, 1H), 1.55-1.88 (m, 5H), 1.95-2.05 (m, 1H), 2.15 (d, J=11.00Hz, 1H), 2.21 (d, J=14.67Hz, 1H), 2.29 (s, 6H), 2.37 (d, J=15.13Hz, 1H), 2.43 (s, 3H), 2.44-2.50 (m, 1H), 2.57 (q, J=6.72Hz, 1H), 2.66-2.77 (m, 2H), 2.98 (t, J=9.63Hz, 1H), 3.05 (d, J=13.76Hz, 1H), 3.18-3.25 (m, 1H), 3.34 (s, 3H), 3.41-3.51 (m, 1H), 3.62 (d, J=7.79Hz, 1H), 3.97-4.04 (m, 2H), 4.39 (d, J=7.34Hz, 1H), 4.61-4.65 (m, 1H), 4.80 (d, J=4.59Hz, 1H), 6.04 (br.s., 1H)

Syntheses of Examples 207 to 213

[0723] Preparation methods of compounds represented by the formula (L) having R^{1 L}, R ^{2 L} and R^{3 L} defined in Table 5 are shown below.

[Table 5-1]

[0724] 

Table 5

Example	R1L	R2L	R3L	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
207		H	Et	692.5	(600 MHz) : 0.90 (t, J=7.34 Hz, 3 H) 0.97 (d, J=6.88 Hz, 2 H) 1.05 (d, J=6.42 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.20 (m, 2 H) 1.16 (d, J=6.42 Hz, 3 H) 1.22 (d, J=6.42 Hz, 3 H) 1.28 (s, 3 H) 1.39 (d, J=15.13 Hz, 1 H) 1.48 - 1.81 (m, 4 H) 1.96 - 2.03 (m, 1 H) 2.05 - 2.11 (m, 1 H) 2.26 (s, 6 H) 2.31 - 2.38 (m, 1 H) 2.72 - 2.80 (m, 1 H) 3.02 (dd, J=15.13, 9.63 Hz, 1 H) 3.11 (dd, J=10.09, 7.34 Hz, 1 H) 3.13 - 3.19 (m, 1 H) 3.21 (s, 3 H) 3.54 (dd, J=10.09, 2.75 Hz, 1 H) 3.62 - 3.73 (m, J=2.75 Hz, 2 H) 3.69 (d, J=2.75 Hz, 2 H) 3.79 (d, J=4.59 Hz, 2 H) 3.95 (d, J=7.34 Hz, 1 H) 4.96 - 5.02 (m, 1 H) 5.20 (d, J=10.55 Hz, 1 H) 7.28 (dd, J=7.79, 4.13 Hz, 1 H) 7.71 (dt, J=8.14, 1.95, 1.83 Hz, 1 H) 8.53 (dd, J=5.04, 1.38 Hz, 1 H) 8.54 (d, J=1.83 Hz, 1 H)
208		H	Et	692.5	(600 MHz) : 0.90 (t, J=7.57 Hz, 3 H) 1.05 (t, 9 H) 1.08 - 1.25 (m, 2 H) 1.17 (d, J=5.96 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.29 (s, 3 H) 1.41 (d, J=14.67 Hz, 1 H) 1.49 - 1.66 (m, 3 H) 1.96 - 2.03 (m, 1 H) 2.05 - 2.12 (m, 1 H) 2.29 (s, 6 H) 2.49 - 2.57 (m, 1 H) 2.73 - 2.79 (m, 1 H) 3.01 (dd, J=15.13, 9.63 Hz, 1 H) 3.15 (dd, J=10.32, 7.11 Hz, 1 H) 3.22 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.53 (dd, J=10.32, 2.52 Hz, 1 H) 3.67 - 3.73 (m, 2 H) 3.84 (d, J=4.58 Hz, 1 H) 3.90 (d, J=3.21 Hz, 2 H) 4.11 (d, J=7.34 Hz, 1 H) 4.96 - 5.02 (m, 1 H) 5.20 (d, J=10.55 Hz, 1 H) 7.18 - 7.21 (m, 1 H) 7.34 (d, J=7.79 Hz, 1 H) 7.66 (dt, J=7.57, 1.83 Hz, 1 H) 8.51 - 8.53 (m, 1 H)

[0725] 

[Table 5-2]

209	cladinosyl	H	Et	731.5	(500 MHz) : 0.92 (t, J=7.62 Hz, 3 H) 1.07 (d, J=7.62 Hz, 3 H) 1.07 (d, J=6.70 Hz, 3 H) 1.17 (d, J=7.31 Hz, 3 H) 1.17 - 1.30 (m, 2 H) 1.22 (d, J=6.10 Hz, 3 H) 1.24 (s, 3 H) 1.25 (d, J=6.40 Hz, 3 H) 1.29 (d, J=6.40 Hz, 3 H) 1.37 (s, 3 H) 1.44 - 1.68 (m, 5 H) 1.75 - 1.82 (m, 1 H) 2.05 - 2.12 (m, 1 H) 2.27 (s, 3 H) 2.27 (s, 6 H) 2.66 - 2.73 (m, 1 H) 2.98 - 3.10 (m, 2 H) 3.16 (dd, J=10.21, 7.16 Hz, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.42 - 3.48 (m, 1 H) 3.58 (dd, J=10.21, 3.50 Hz, 1 H) 3.66 (d, J=7.92 Hz, 1 H) 3.74 - 3.79 (m, 1 H) 3.89 - 3.92 (m, 1 H) 3.95 (d, J=8.23 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.35 (d, J=7.31 Hz, 1 H) 4.81 - 4.86 (m, 1 H) 4.89 (d, J=4.57 Hz, 1 H)
210		H		930.6	(300 MHz): 0.81 - 1.40 (m, 17 H) 1.13 (d, J=7.31 Hz, 3 H) 1.32 (d, J=6.22 Hz, 3 H) 1.36 (s, 3 H) 1.41 - 1.81 (m, 5 H) 1.97 - 2.12 (m, 2 H) 2.21 - 2.51 (m, 3 H) 2.28 (s, 6 H) 2.61 - 2.73 (m, 1 H) 2.78 - 2.92 (m, 1 H) 2.99 - 3.72 (m, 8 H) 3.12 (s, 3 H) 3.30 (s, 3 H) 3.60 (s, 2 H) 3.79 - 3.86 (m, 1 H) 3.89 (d, J=7.62 Hz, 1 H) 4.00 (d, 1 H) 4.34 (d, J=6.99 Hz, 1 H) 4.81 (d, J=4.35 Hz, 1 H) 4.82 - 4.91 (m, 1 H) 6.15 - 6.23 (m, 1 H) 6.47 (dd, J=3.34, 1.79 Hz, 1 H) 6.67 (d, J=2.49 Hz, 1 H) 7.19 (d, J=7.46 Hz, 1 H) 7.35 (t, J=7.93 Hz, 1 H) 7.46 (d, J=1.55 Hz, 1 H) 7.55 - 7.61 (m, 2 H)
211				770.5	(300 MHz) : 1.05 (d, J=6.84 Hz, 3 H) 1.12 - 1.91 (m, 15 H) 1.29 (s, 3 H) 1.39 (d, J=6.99 Hz, 3 H) 2.02 - 2.16 (m, 1 H) 2.27 (s, 6 H) 2.40 - 2.52 (m, 1 H) 2.69 - 3.08 (m, 4 H) 3.14 - 3.23 (m, 1 H) 3.46 - 3.68 (m, 3 H) 3.59 (s, 3 H) 3.65 (s, 2 H) 3.72 - 3.81 (m, 1 H) 3.97 - 4.06 (m, 2 H) 4.32 (d, J=7.77 Hz, 1 H) 4.87 - 4.98 (m, 1 H) 6.17 - 6.23 (m, 1 H) 6.47 (dd, J=3.11, 2.02 Hz, 1 H) 6.68 (d, J=2.80 Hz, 1 H) 7.17 - 7.22 (m, 1 H) 7.36 (t, J=7.77 Hz, 1 H) 7.46 - 7.48 (m, 1 H) 7.55 - 7.61 (m, 2 H)
212	cladinosyl	H		930.5	(600 MHz): 1.03 - 1.07 (m, 6 H) 1.14 (d, J=7.34 Hz, 3 H) 1.15 - 1.27 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.23 (s, 3 H) 1.25 (s, 3 H) 1.28 (d, J=5.96 Hz, 3 H) 1.36 (s, 3 H) 1.47 (d, J=16.51 Hz, 1 H) 1.51 (dd, J=15.13, 5.04 Hz, 1 H) 1.54 - 1.84 (m, 6 H) 2.02 - 2.12 (m, 1 H) 2.20 - 2.37 (m, 8 H) 2.66 - 2.75 (m, 1 H) 3.01 (t, J=9.86 Hz, 1 H) 3.08 (dd, J=15.13, 9.63 Hz, 1 H) 3.13 - 3.22 (m, 1 H) 3.20 (s, 3 H) 3.29 (s, 3 H) 3.35 - 3.51 (m, 3 H) 3.59 (dd, J=10.09, 3.67 Hz, 1 H) 3.66 (d, J=7.79 Hz, 1 H) 3.74 - 3.79 (m, 1 H) 3.85 - 3.91 (m, 1 H) 3.93 (d, J=7.79 Hz, 1 H) 3.95 - 4.03 (m, 1 H) 4.35 (d, J=6.88 Hz, 1 H) 4.85 (d, J=4.59 Hz, 1 H) 4.89 (s, 1 H) 6.48 (dd, J=3.67, 1.83 Hz, 1 H) 6.49 - 6.53 (m, 1 H) 6.73 - 6.76 (m, 1 H) 7.42 (t, J=7.79 Hz, 1 H) 7.47 (d, J=1.83 Hz, 1 H) 7.62 - 7.66 (m, 1 H) 7.75 - 7.79 (m, 1 H) 8.03 - 8.07 (m, 1 H)

[0726] 

[Table 5-3]

213

770.5

(600 MHz) : 1.04 (d, J=6.88 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.21 - 1.29 (m, 11 H) 1.35 (d, J=6.88 Hz, 3 H) 1.45 - 1.79 (m, 6 H) 2.08 - 2.20 (m, 1 H) 2.27 (s, 6 H) 2.38 - 2.53 (m, 1 H) 2.76 (s, 3 H) 2.86 - 2.95 (m, 1 H) 3.04 (dd, J=15.13, 10.55 Hz, 1 H) 3.13 - 3.23 (m, 1 H) 3.35 - 3.53 (m, 2 H) 3.53 - 3.81 (m, 4 H) 4.00 - 4.11 (m, 2 H) 4.29 (d, J=7.34 Hz, 1 H) 4.83 - 4.90 (m, 1 H) 6.47 (dd, J=3.67, 1.83 Hz, 1 H) 6.48 - 6.55 (m, 1 H) 6.77 (d, J=4.13 Hz, 1 H) 7.41 (t, J=7.79 Hz, 1 H) 7.45 - 7.49 (m, 1 H) 7.61 - 7.65 (m, 1 H) 7.74 - 7.78 (m, 1 H) 8.04 - 8.07 (m, 1 H)

Example 207

[0727] 

(1) The compound obtained in Example 125, (2) (74 mg) and pyridine (83 µl) were dissolved in chloroform, the solution was added with triphosgene (91 mg), and the mixture was stirred at room temperature for 9 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a 9,10a-cyclic carbamate compound (52 mg).

(2) By using the compound obtained in (1) mentioned above (52 mg) as a starting material, the compound shown in Table 5 (40 mg) was obtained in the same manner as that of Example 125, (3).

Example 208

[0728] By using the compound obtained in Example 112 (97 mg) as a starting material, the compound shown in Table 5 (19 mg) was obtained in the same manners as those of Example 176, (3), Example 207, (1) and Example 125, (3).

Example 209

[0729] 

(1) By using the compound obtained in Example 176, (3) (50 mg) as a starting material, a 9,10a-cyclic carbamate compound (14.4 mg) was obtained in the same manner as that of Example 207, (1).

(2) By using the compound obtained in (1) mentioned above as a starting material, the compound shown in Table 5 (5.0 mg) was obtained in the same manner as that of Example 176, (5).

Example 210

[0730] 

(1) By using the compound obtained in Example 23 (32 mg) as a starting material, a 9,10a-cyclic carbamate compound (10.5 mg) was obtained in the same manners as those of Example 176, (3) and Example 207 (1).

(2) By using the compound obtained in (1) mentioned above (10.5 mg) as a starting material, the compound shown in Table 5 (4.4 mg) was obtained in the same manner as that of Example 125, (3).

Example 211

[0731] 

(1) The compound obtained in Example 210, (1) (32 mg) was dissolved in 1 N hydrochloric acid (1 ml) and ethanol (1 ml), and the solution was stirred at room temperature for 18 hours. The reaction mixture was neutralized with 1 N aqueous sodium hydroxide, and then extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1), and by using the resulting compound (7.5 mg) as a starting material, a 2'-O-acetyl compound (7.4 mg) was obtained in the same manner as that of Example 113, (2).

(2) By using the compound obtained in (1) mentioned above (7.4 mg) as a starting material, the compound shown in Table 5 (5.0 mg) was obtained in the same manner as that of Example 125, (3).

Example 212

[0732] 

(1) By using the compound obtained in Example 38 (82 mg) as a starting material, a 9,10a-cyclic carbamate compound (23.0 mg) was obtained in the same manners as those of Example 176, (3) and Example 207, (1).

(3) By using the compound obtained in (2) mentioned above (5.0 mg) as a starting material, the compound shown in Table 5 (2.8 mg) was obtained in the same manner as that of Example 125, (3).

Example 213

[0733] By using the compound obtained in Example 212, (1) (17 mg) as a starting material, the compound shown in Table 5 (2.5 mg) was obtained in the same manners as those of Example 211, (1) and Example 125, (3).

Syntheses of Examples 214 to 235

[0734] Preparation methods of compounds represented by the formula (M) having R¹M , R2 M , and R3 M defined in Table 6 are shown below.

[Table 6-1]

[0735] 

Table 6

R2M in the compounds represented by the formula (M) is cladinosyl group except for the compound of Example 218. R2M in the compound of Example 218 is a group represented by the formula:

Example	R1M	R3M	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
214	Et	H	732.5	(300 MHz) : 0.89 (t, J=7.54 Hz, 3 H) 1.06 (d, J=6.84 Hz, 3 H) 1.10 (d, J=7.46 Hz, 3 H) 1.20 (t, 16 H) 1.30 (s, 3 H) 1.46 - 1.72 (m, 5 H) 1.89 - 2.77 (m, 8 H) 2.11 (s, 3 H) 2.28 (s, 6 H) 2.96 - 3.06 (m, 1 H) 3.25 - 3.30 (m, 1 H) 3.27 (s, 3 H) 3.34 (s, 3 H) 3.44 - 3.62 (m, 3 H) 3.68 (d, J=6.99 Hz, 1 H) 3.92 (dd, J=5.28, 1.55 Hz, 1 H) 3.96 - 4.08 (m, 1 H) 4.48 (d, J=7.46 Hz, 1 H) 4.80 - 4.92 (m, 1 H) 4.89 (d, J=4.97 Hz, 1 H)
215	H	H	704.4	(300 MHz) : 1.03 - 1.40 (m, 16 H) 1.05 (d, J=6.99 Hz, 3 H) 1.11 (d, J=7.77 Hz, 3 H) 1.28 (s, 3 H) 1.48 - 1.70 (m, 5 H) 1.97 - 2.54 (m, 5 H) 2.19 (s, 3 H) 2.29 (s, 6 H) 2.63 - 2.91 (m, 3 H) 3.01 (t, J=9.64 Hz, 1 H) 3.23 - 3.37 (m, 1 H) 3.25 (s, 3 H) 3.34 (s, 3 H) 3.47 - 3.59 (m, 1 H) 3.63 - 3.74 (m, 2 H) 3.94 - 4.06 (m, 2 H) 4.20 - 4.31 (m, 1 H) 4.50 (d, J=7.31 Hz, 1 H) 4.66 (d, J=4.35 Hz, 1 H)

[0736] 

[Table 6-2]

216		H	931.7	(300 MHz) : 1.00 - 1.17 (m, 12 H) 1.23 (d, J=6.37 Hz, 3 H) 1.24 - 1.29 (m, 1 H) 1.26 (s, 3 H) 1.26 - 1.29 (m, 3 H) 1.32 (s, 3 H) 1.38 - 1.74 (m, 5 H) 2.04 - 2.24 (m, 3 H) 2.17 (s, 3 H) 2.30 (s, 6 H) 2.32 - 2.57 (m, 3 H) 2.64 - 2.95 (m, 3 H) 3.02 (t, J=9.79 Hz, 1 H) 3.25 (s, 3 H) 3.30 - 3.33 (m, 1 H) 3.33 (s, 3 H) 3.39 (d, J=7.15 Hz. 1 H) 3.43 - 3.62 (m, 3 H) 3.58 (s, 2 H) 3.66 (d, J=6.22 Hz, 1 H) 3.80 (d, J=7.15 Hz, 1 H) 3.95 - 4.08 (m, 1 H) 4.45 (d, J=7.31 Hz, 1 H) 4.60 (s, 1 H) 4.86 (d, J=4.66 Hz, 1 H) 6.23 (s, 1 H) 6.46 (dd, J=3.42, 1.87 Hz, 1 H) 6.68 (dd, J=3.26, 0.78 Hz, 1 H) 7.15 - 7.22 (m, 1 H) 7.35 (t, J=7.69 Hz, 1 H) 7.44 - 7.48 (m, 1 H) 7.54 - 7.62 (m, 2 H)
217		H	931.4	(600 MHz) : 1.07 - 1.15 (m, 6 H) 1.16 - 1.21 (m, 6 H) 1.25 (d, J=5.96 Hz, 3 H) 1.26 - 1.32 (m, 7 H) 1.35 - 1.36 (m, 3 H) 1.46 - 1.88 (m, 7 H) 2.01 - 2.06 (m, 1 H) 2.15 - 2.35 (m, 1 H) 2.26 - 2.30 (m, 3 H) 2.31 - 2.32 (m, 6 H) 2.36 - 2.52 (m, 2 H) 2.68 - 2.82 (m, 3 H) 3.04 (t, J=9.63 Hz, 1 H) 3.24 - 3.42 (m, 1 H) 3.26 - 3.28 (m, 3 H) 3.35 - 3.36 (m, 3 H) 3.42 - 3.49 (m, 1 H) 3.49 - 3.58 (m, 1 H) 3.59 - 3.81 (m, 3 H) 3.68 (d, J=8.71 Hz, 1 H) 3.85 - 3.89 (m, 1 H) 4.02 - 4.09 (m, 1 H) 4.48 (d, J=7.34 Hz, 1 H) 4.71 (s, 1 H) 4.89 - 4.93 (m, 1 H) 6.50 - 6.54 (m, 1 H) 6.78 (d, J=2.75 Hz, 1 H) 7.13 - 7.18 (m, 1 H) 7.39 - 7.43 (m, 1 H) 7.44 - 7.53 (m, 3 H)
218	Et	H	693.6	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.97 - 1.25 (m, 8 H) 0.99 (d, J=6.88 Hz, 3 H) 1.08 (d, J=6.88 Hz, 3 H) 1.15 (d, J=6.42 Hz, 3 H) 1.27 (s, 3 H) 1.42 - 1.66 (m, 3 H) 1.97 - 2.05 (m, 1 H) 2.25 (s, 3 H) 2.30 (s, 6 H) 2.44 - 2.64 (m, 3 H) 2.68 - 2.73 (m, 1 H) 2.75 - 2.81 (m, 1 H) 3.12 (s, 3 H) 3.21 (dd, J=10.09, 7.34 Hz, 1 H) 3.24 - 3.28 (m, 1 H) 3.33 - 3.39 (m, 1 H) 3.40 - 3.47 (m, 1 H) 3.72 (d, J=4.13 Hz, 1 H) 3.87 - 3.96 (m, 2 H) 4.11 (d, J=7.34 Hz, 1 H) 4.86 - 4.93 (m, 1 H) 5.11 (d, J=11.00 Hz, 1 H) 7.18 (dd, J=7.79, 4.13 Hz, 1 H) 7.36 (d, J=8.25 Hz, 1 H) 7.66 (td, J=7.57, 1.83 Hz, 1 H) 8.52 (d, J=4.58 Hz, 1 H)
219		H	817.7	(500 MHz) : 1.04 - 1.09 (m, 6 H) 1.11 (d, J=6.86 Hz, 3 H) 1.15 (d, J=7.13 Hz, 3 H) 1.19 - 1.33 (m, 7 H) 1.21 (d, J=6.31 Hz, 3 H) 1.30 (s, 3 H) 1.45 - 1.74 (m, 3 H) 1.94 - 2.10 (m, 2 H) 2.13 - 2.23 (m, 4 H) 2.29 (s, 6 H) 2.37 (d, J=15.08 Hz, 1 H) 2.42 - 2.52 (m, 1 H) 2.57 - 2.67 (m, 1 H) 2.68 - 2.75 (m, 1 H) 2.78 - 2.85 (m, 1 H) 3.00 (t, J=9.87 Hz, 1 H) 3.14 - 3.36 (m, 2 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.39 - 3.60 (m, 4 H) 3.65 (d, J=7.13 Hz, 1 H) 3.86 (d, J=6.03 Hz, 1 H) 3.95 - 4.05 (m, 1 H) 4.45 (d, J=7.13 Hz, 1 H) 4.50 - 4.62 (m, 2 H) 4.73 - 4.86 (m, 2 H) 5.12 - 5.23 (m, 2 H) 5.29 (d, J=16.45 Hz, 1 H) 5.82 - 5.99 (m, 1 H)

[0737] 

[Table 6-3]

220		H	867.8	(600 MHz) : 1.01 - 1.08 (m, 6 H) 1.08 - 1.16 (m, 6 H) 1.18 - 1.56 (m, 4 H) 1.20 - 1.26 (m, 9 H) 1.29 (s, 3 H) 1.96 - 2.07 (m, 2 H) 2.13 - 2.17 (m, 6 H) 2.21 - 2.48 (m, 6 H) 2.58 - 2.84 (m, 2 H) 2.96 - 3.05 (m, 1 H) 3.22 (s, 3 H) 3.24 - 3.33 (m, 1 H) 3.31 - 3.32 (m, 3 H) 3.36 - 3.59 (m, 5 H) 3.65 (d, J=7.34 Hz, 1 H) 3.82 - 3.87 (m, 1 H) 3.95 - 4.02 (m, 1 H) 4.46 (d, J=7.34 Hz, 1 H) 4.77 - 4.87 (m, 2 H) 5.09 (d, J=4.58 Hz, 2 H) 5.16 (s, 1 H) 7.29 - 7.38 (m, 5 H)
221		H	852.7	(600 MHz) : 1.04 (d, J=6.42 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.12 (d, J=6.88 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.28 (m, 4 H) 1.23 (s, 3 H) 1.29 (s, 3 H) 1.51 - 1.69 (m, 7 H) 1.90 - 1.96 (m, 1 H) 1.99 - 2.05 (m, 1 H) 2.10 (s, 3 H) 2.15 (d, J=10.55 Hz, 1 H) 2.29 (s, 6 H) 2.30 - 2.35 (m, 1 H) 2.37 (d, J=15.13 Hz, 1 H) 2.43 - 2.52 (m, 1 H) 2.56 - 2.62 (m, 1 H) 2.65 - 2.74 (m, 2 H) 3.00 (t, J=9.86 Hz, 1 H) 3.25 (s, 3 H) 3.26 - 3.33 (m, 2 H) 3.32 (s, 3 H) 3.42 - 3.49 (m, 2 H) 3.49 - 3.54 (m, 1 H) 3.54 - 3.60 (m, 1 H) 3.67 (d, J=6.88 Hz, 1 H) 3.88 - 3.91 (m, 1 H) 3.99 - 4.02 (m, 1 H) 4.47 (d, J=7.34 Hz, 1 H) 4.48 (s, 2 H) 4.88 (d, J=4.59 Hz, 1 H) 4.88 - 4.94 (m, 1 H) 7.26 - 7.36 (m, 5 H)
222		H	762.7	(600 MHz) : 1.05 - 1.09 (m, 6 H) 1.12 (d, J=6.88 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.17 - 1.29 (m, 7 H) 1.21 (d, J=5.96 Hz, 3 H) 1.30 (s, 3 H) 1.50 - 1.74 (m, 7 H) 1.99 - 2.10 (m, 2 H) 2.16 (s, 3 H) 2.21 - 2.25 (m, 1 H) 2.30 (s, 6 H) 2.37 (d, J=15.13 Hz, 1 H) 2.45 - 2.60 (m, 2 H) 2.68 - 2.74 (m, 1 H) 2.76 - 2.83 (m, 1 H) 3.00 (t, J=9.63 Hz, 1 H) 3.24 (s, 3 H) 3.29 - 3.31 (m, 1 H) 3.32 (s, 3 H) 3.43 - 3.48 (m, 1 H) 3.49 - 3.54 (m, 1 H) 3.54 - 3.60 (m, 1 H) 3.61 - 3.70 (m, 3 H) 3.87 (d, J=5.50 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.46 (d, J=6.88 Hz, 1 H) 4.80 - 4.85 (m, 1 H) 4.87 (d, J=4.58 Hz, 1 H)
223	Et		772.8	(500 MHz) : 0.87 (t, J=7.26 Hz, 3 H) 1.04 (d, J=6.88 Hz, 3 H) 1.07 (d, J=7.65 Hz, 3 H) 1.10 (d, J=6.88 Hz, 3 H) 1.15 (d, J=6.88 Hz, 3 H) 1.24 (d, 13 H) 1.58 (d, 5 H) 1.90 (d, J=14.53 Hz, 1 H) 2.00 - 2.05 (m, 1 H) 2.10 (s, 3 H) 2.27 (s, 6 H) 2.37 (d, J=15.29 Hz, 1 H) 2.42 - 2.49 (m, 1 H) 2.52 - 2.60 (m, 1 H) 2.65 - 2.74 (m, 2 H) 2.99 (d, J=9.17 Hz, 1 H) 3.20 (s, 3 H) 3.26 - 3.34 (m, 1 H) 3.32 (s, 3 H) 3.40 - 3.47 (m, 1 H) 3.47 - 3.60 (m, 2 H) 3.66 (d, J=6.88 Hz, 1 H) 3.88 (d, J=3.06 Hz, 1 H) 3.96 - 4.05 (m, 1 H) 4.46 (d, J=6.88 Hz, 1 H) 4.49 (d, J=4.59 Hz, 2 H) 4.74 - 4.86 (m, 1 H) 4.88 (d, J=4.59 Hz, 1 H) 5.12 (d, J=9.94 Hz, 1 H) 5.25 (d, J=16.05 Hz, 1 H) 5.87 - 6.02 (m, 1 H)

[0738] 

[Table 6-4]

224	Et			(600 MHz) : 0.87 (t, J=7.57 Hz, 3 H) 1.06 (d, J=6.88 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.11 (d, J=7.34 Hz, 3 H) 1.12 (m, 1 H) 1.16 (d, J=6.88 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.23 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.27 (s, 3 H) 1.54 - 1.67 (m, 5 H) 1.90 (d, J=14.67 Hz, 1 H) 1.99 - 2.04 (m, 1 H) 2.10 (s, 3 H) 2.29 (s, 6 H) 2.38 (d, J=15.13 Hz, 1 H) 2.45 - 2.51 (m, 1 H) 2.55 - 2.61 (m, 1 H) 2.72 (s, 2 H) 2.95 - 3.02 (m, 3 H) 3.23 (s, 3 H) 3.30 - 3.31 (m, 1 H) 3.32 (s, 3 H) 3.41 - 3.45 (m, 1 H) 3.47 - 3.57 (m, 2 H) 3.67 - 3.68 (m, 1 H) 3.86 - 3.90 (m, 1 H) 3.98 - 4.02 (m, 1 H) 4.03 - 4.10 (m, 2 H) 4.47 (d, J=7.34 Hz, 1 H) 4.81 - 4.84 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H)
225	Et		866.8	(500 MHz) : 0.87 (t, J=7.54 Hz, 3 H) 1.04 (d, J=6.58 Hz, 3 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 (d, J=6.86 Hz, 3 H) 1.16 (d, J=7.13 Hz, 3 H) 1.20 (d, J=6.03 Hz, 3 H) 1.21 - 1.31 (m, 1 H) 1.21 - 1.24 (m, 3 H) 1.23 (s, 3 H) 1.28 (s, 3 H) 1.52 - 1.66 (m, 5 H) 1.92 (d, J=14.54 Hz, 1 H) 2.01 - 2.07 (m, 1 H) 2.11 (s, 3 H) 2.13 - 2.22 (m, 1 H) 2.27 (s, 6 H) 2.38 (d, J=15.08 Hz, 1 H) 2.42 - 2.51 (m, 1 H) 2.52 - 2.61 (m, 1 H) 2.65 - 2.75 (m, 2 H) 2.95 - 3.03 (m, 1 H) 3.20 (s, 3 H) 3.25 - 3.36 (m, 1 H) 3.32 (s, 3 H) 3.38 - 3.47 (m, 1 H) 3.47 - 3.58 (m, 2 H) 3.62 - 3.75 (m, 3 H) 3.89 (d, J=5.48 Hz, 1 H) 3.96 - 4.05 (m, 1 H) 4.12 - 4.22 (m, 2 H) 4.46 (d, J=7.13 Hz, 1 H) 4.50 - 4.58 (m, 2 H) 4.78 - 4.86 (m, 1 H) 4.89 (d, J=4.66 Hz, 1 H) 7.21 - 7.35 (m, 5 H)
226	Et		776.8	(500 MHz) : 0.88 (t, J=7.54 Hz, 3 H) 1.05 (d, J=6.86 Hz, 3 H) 1.07 (d, J=7.40 Hz, 3 H) 1.12 (d, J=6.86 Hz, 3 H) 1.16 (d, J=7.1 Hz, 3 H) 1.18 - 1.36 (m, 13 H) 1.46 - 1.74 (m, 5 H) 1.80 - 1.87 (m, 1 H) 1.96 - 2.03 (m, 1 H) 2.08 (s, 3 H) 2.14 (d, J=10.97 Hz, 1 H) 2.31 (s, 6 H) 2.37 (d, J=15.36 Hz, 1 H) 2.42 - 2.56 (m, 1 H) 2.58 - 2.65 (m, 1 H) 2.65 - 2.74 (m, 2 H) 3.01 (t, J=9.19 Hz, 1 H) 3.26 (s, 3 H) 3.28 - 3.34 (m, 1 H) 3.32 (s, 3 H) 3.42 - 3.59 (m, 3 H) 3.62 - 3.66 (m, 1 H) 3.73 - 3.85 (m, 2 H) 3.87 - 3.92 (m, 1 H) 3.95 - 4.03 (m, 1 H) 4.13 (t, J=4.25 Hz, 2 H) 4.47 (d, J=7.40 Hz, 1 H) 4.79 - 4.86 (m, 1 H) 4.88 (d, J=4.39 Hz, 1 H)
227	Et		803.8	(500 MHz) : 0.87 (t, J=7.54 Hz, 3 H) 1.05 (d, J=6.86 Hz, 3 H) 1.06 - 1.10 (m, 6 H) 1.15 (d, J=7.13 Hz, 3 H) 1.18 - 1.30 (m, 13 H) 1.51 - 1.81 (m, 5 H) 1.84 - 1.95 (m, 1 H) 1.97 - 2.08 (m, 1 H) 2.11 (s, 3 H) 2.15 (d, J=9.87 Hz, 1 H) 2.23 - 2.34 (m, 12 H) 2.38 (d, J=15.63 Hz, 1 H) 2.42 - 2.51 (m, 1 H) 2.52 - 2.76 (m, 5 H) 3.00 (t, J=10.56 Hz, 1 H) 3.20 (s, 3 H) 3.27 - 3.35 (m, 1 H) 3.33 (s, 3 H) 3.40 - 3.47 (m, 1 H) 3.47 - 3.57 (m, 2 H) 3.67 (d, J=6.86 Hz, 1 H) 3.88 (d, J=6.58 Hz, 1 H) 3.94 - 4.05 (m, 1 H) 4.07 - 4.19 (m, 2 H) 4.47 (d, J=7.13 Hz, 1 H) 4.77 - 4.86 (m, 1 H) 4.89 (d, J=4.66 Hz, 1 H)

[0739] 

[Table 6-5]

228	Et		880.8	(500 MHz) : 0.87 (t, J=7.54 Hz, 3 H) 1.01 (d, J=6.86 Hz, 3 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 (d, J=7.13 Hz, 3 H) 1.16 (d, J=7.13 Hz, 3 H) 1.21 (d, J=6.31 Hz, 3 H) 1.20 - 1.30 (m, 1 H) 1.23 (s, 3 H) 1.25 (d, J=6.31 Hz, 3 H) 1.28 (s, 3 H) 1.49 - 1.72 (m, 5 H) 1.93 - 2.08 (m, 2 H) 2.10 (s, 3 H) 2.16 (d, J=10.42 Hz, 1 H) 2.30 (br. s., 6 H) 2.37 (d, J=14.81 Hz, 1 H) 2.43 - 2.59 (m, 2 H) 2.64 - 2.75 (m, 2 H) 3.00 (t, J=9.87 Hz, 1 H) 3.21 (s, 3 H) 3.27 - 3.35 (m, 1 H) 3.32 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.46 - 3.57 (m, 2 H) 3.66 (d, J=6.86 Hz, 1 H) 3.89 (d, J=5.48 Hz, 1 H) 3.96 - 4.05 (m, 1 H) 4.46 (d, J=7.13 Hz, 1 H) 4.59 (d, J=3.29 Hz, 2 H) 4.76 - 4.86 (m, 1 H) 4.89 (d, J=4.39 Hz, 1 H) 5.12 - 5.21 (m, 2 H) 7.27 - 7.37 (m, 5 H)
229	Et		789.8	(500 MHz) : 0.88 (t, J=7.26 Hz, 3 H) 1.04 - 1.10 (m, 6 H) 1.11 (d, J=6.88 Hz, 3 H) 1.16 (d, J=6.88 Hz, 3 H) 1.19 - 1.38 (m, 13 H) 1.51 - 1.61 (m, 3 H) 1.61 - 1.72 (m, 2 H) 1.74 - 1.82 (m, 2 H) 1.86 - 1.93 (m, 1 H) 2.01 - 2.07 (m, 1 H) 2.14 (s, 3 H) 2.29 (s, 6 H) 2.38 (d, J=15.29 Hz, 1 H) 2.44 - 2.52 (m, 1 H) 2.53 - 2.60 (m, 1 H) 2.66 - 2.75 (m, 2 H) 2.77 - 2.84 (m, 2 H) 3.00 (d, J=9.17 Hz, 1 H) 3.22 (s, 3 H) 3.26 - 3.34 (m, 1 H) 3.33 (s, 3 H) 3.35 - 3.40 (m, 1 H) 3.40 - 3.47 (m, 1 H) 3.47 - 3.57 (m, 1 H) 3.67 (d, J=6.88 Hz, 1 H) 3.89 (d, J=6.12 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.04 - 4.11 (m, 2 H) 4.45 (d, J=6.88 Hz, 1 H) 4.77 - 4.86 (m, 1 H) 4.90 (d, J=4.59 Hz, 1 H)
230	Et		790.7	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 1.05 (d, J=7.34 Hz, 3 H) 1.07 (d, J=6.42 Hz, 3 H) 1.13 (d, J=6.88 Hz, 3 H) 1.15 (d, J=6.88 Hz, 3 H) 1.19 - 1.36 (m, 13 H) 1.48 - 1.59 (m, 3 H) 1.72 - 1.87 (m, 2 H) 1.89 - 1.97 (m, 1 H) 1.99 - 2.06 (m, 1 H) 2.16 (s, 6 H) 2.35 (d, J=15.13 Hz, 1 H) 2.49 - 2.59 (m, 1 H) 2.54 (s, 3 H) 2.67 - 2.77 (m, 2 H) 2.83 - 2.92 (m, 1 H) 2.99 (d, J=9.17 Hz, 1 H) 3.25 (s, 3 H) 3.26 - 3.43 (m, 3 H) 3.30 (s, 3 H) 3.49 - 3.58 (m, 1 H) 3.61 - 3.64 (m, 1 H) 3.86 (d, J=6.88 Hz, 1 H) 3.93 - 4.02 (m, 1 H) 4.40 - 4.52 (m, 3 H) 4.80 - 4.86 (m, 1 H) 4.87 (d, J=4.59 Hz, 1 H)
231	Et		958.6	(500 MHz) : 0.84 (t, J=7.54 Hz, 3 H) 1.04 (d, J=6.86 Hz, 3 H) 1.09 (d, J=7.40 Hz, 3 H) 1.11 (d, J=7.13 Hz, 3 H) 1.16 (d, J=7.13 Hz, 3 H) 1.19 (d, J=6.03 Hz, 3 H) 1.21 - 1.30 (m, 7 H) 1.31 (s, 3 H) 1.45 - 1.71 (m, 5 H) 1.94 - 2.20 (m, 8 H) 2.20 - 2.34 (m, 7 H) 2.37 (d, J=20.02 Hz, 1 H) 2.41 - 2.51 (m, 1 H) 2.72 - 2.77 (m, 2 H) 2.98 - 3.03 (m, 1 H) 3.09 - 3.13 (m, 2 H) 3.16 - 3.27 (m, 1 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.60 (m, 5 H) 3.68 (d, J=7.13 Hz, 1 H) 3.83 (d, J=5.76 Hz, 1 H) 3.96 - 4.04 (m, 1 H) 4.45 (d, J=7.13 Hz, 1 H) 4.51 (d, J=2.47 Hz, 2 H) 4.66 - 4.77 (m, 1 H) 4.90 (d, J=4.66 Hz, 1 H) 6.52 - 6.60 (m, 1 H) 7.27 (d, J=4.66 Hz, 1 H) 7.51 - 7.58 (m, 1 H) 7.69 (t, J=7.68 Hz, 1 H) 8.02 (d, J=9.87 Hz, 1 H) 8.09 (d, J=9.05 Hz, 1 H) 8.80 (d, J=4.39 Hz, 1 H)

[0740] 

[Table 6-6]

232	Et		948.9	(500 MHz) : 0.88 (t, J=7.65 Hz, 3 H) 1.04 (d, J=6.88 Hz, 3 H) 1.06 - 1.10 (m, 6 H) 1.16 (d, J=6.88 Hz, 3 H) 1.20 - 1.31 (m, 13 H) 1.49 - 1.72 (m, 5 H) 1.86 - 1.95 (m, 1 H) 1.99 - 2.07 (m, 1 H) 2.10 (s, 3 H) 2.15 (d, J=10.70 Hz, 1 H) 2.29 (br. s., 6 H) 2.38 (d, J=15.29 Hz, 1 H) 2.41 - 2.52 (m, 1 H) 2.53 - 2.61 (m, 1 H) 2.66 - 2.75 (m, 2 H) 2.88 - 2.96 (m, 4 H) 3.00 (t, J=9.94 Hz, 1 H) 3.20 (s, 3 H) 3.28 - 3.36 (m, 1 H) 3.33 (s, 3 H) 3.38 - 3.44 (m, 1 H) 3.44 - 3.58 (m, 2 H) 3.66 (d, J=6.88 Hz, 1 H) 3.79 (t, J=6.50 Hz, 2 H) 3.89 (d, J=3.82 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.04 - 4.12 (m, 2 H) 4.46 (d, J=7.65 Hz, 1 H) 4.75 - 4.86 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 7.69 (dd, J=5.35, 3.06 Hz, 2 H) 7.83 (dd, J=5.35, 3.06 Hz, 2 H)
233	Et		1122.0	(600 MHz) : 0.84 (t, J=7.57 Hz, 3 H) 1.13 (m, 22 H) 1.13 (d, J=6.88 Hz, 3 H) 1.46 - 1.61 (m, 5 H) 1.75 - 2.38 (m, 13 H) 2.39 - 2.62 (m, 2 H) 2.62 - 2.71 (m, 2 H) 2.79 - 2.94 (m, 6 H) 2.98 (t, J=9.40 Hz, 1 H) 3.15 (s, 3 H) 3.23 - 3.56 (m, 4 H) 3.29 (s, 3 H) 3.61 - 3.63 (m, 1 H) 3.69 (t, J=6.88 Hz, 4 H) 3.81 - 3.87 (m, 1 H) 3.91 - 4.03 (m, 3 H) 4.40 - 4.48 (m, 1 H) 4.73 - 4.82 (m, 1 H) 4.86 (d, J=4.58 Hz, 1 H) 7.59 - 7.66 (m, 4 H) 7.66 - 7.72 (m, 4 H)
234	Et		818.8	(500 MHz) : 0.88 (t, J=7.45 Hz, 3 H) 1.03 - 1.10 (m, 6 H) 1.11 (d, J=6.88 Hz, 3 H) 1.17 (d, J=7.26 Hz, 3 H) 1.20 - 1.33 (m, 7 H) 1.22 (d, J=6.12 Hz, 3 H) 1.29 (s, 3 H) 1.50 - 1.60 (m, 3 H) 1.61 - 1.69 (m, 2 H) 1.73 - 2.08 (m, 2 H) 2.13 (s, 3 H) 2.30 (s, 6 H) 2.38 (d, J=14.91 Hz, 1 H) 2.44 - 2.51 (m, 1 H) 2.52 - 2.60 (m, 1 H) 2.67 - 2.79 (m, 4 H) 2.79 - 2.85 (m, 2 H) 2.85 - 2.97 (m, 2 H) 3.00 (d, J=9.17 Hz, 1 H) 3.24 (s, 3 H) 3.26 - 3.34 (m, 1 H) 3.33 (s, 3 H) 3.35 - 3.60 (m, 3 H) 3.67 (d, J=6.88 Hz, 1 H). 3.89 (d, J=5.73 Hz, 1 H) 3.97 - 4.05 (m, 1 H) 4.11 - 4.17 (m, 2 H) 4.45 (d, J=7.26 Hz, 1 H) 4.77 - 4.87 (m, 1 H) 4.90 (d, J=4.59 Hz, 1 H)
235	Et		817.9	(500 MHz) : 0.88 (t, J=7.26 Hz, 3 H) 1.04 - 1.10 (m, 6 H) 1.11 (d, J=6.88 Hz, 3 H) 1.16 (d, J=6.88 Hz, 3 H) 1.19 - 1.38 (m, 13 H) 1.51 - 1.61 (m, 3 H) 1.61 - 1.72 (m, 2 H) 1.74 - 1.82 (m, 2 H) 1.86 - 1.93 (m, 1 H) 2.01 - 2.07 (m, 1 H) 2.14 (s, 3 H) 2.29 (s, 6 H) 2.38 (d, J=15.29 Hz, 1 H) 2.44 - 2.52 (m, 1 H) 2.53 - 2.60 (m, 1 H) 2.66 - 2.75 (m, 2 H) 2.77 - 2.84 (m, 2 H) 3.00 (d, J=9.17 Hz, 1 H) 3.22 (s, 3 H) 3.26 - 3.34 (m, 1 H) 3.33 (s, 3 H) 3.35 - 3.40 (m, 1 H) 3.40 - 3.47 (m, 1 H) 3.47 - 3.57 (m, 1 H) 3.67 (d, J=6.88 Hz, 1 H) 3.89 (d, J=6.12 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.04 - 4.11 (m, 2 H) 4.45 (d, J=6.88 Hz, 1 H) 4.77 - 4.86 (m, 1 H) 4.90 (d, J=4.59 Hz, 1 H)

Example 214

[0741] The compound obtained in Example 176 (285 mg) was dissolved in methanol (10 ml), the solution was added with imidazole (163 mg) and hydroxylamine hydrochloride (138 mg), and the mixture was stirred for 4 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was washed with saturated aqueous ammonium chloride, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1 to 10:1:0.1) to obtain the compound shown in Table 6 (160 mg).

Example 215

[0742] By using the compound obtained in Example 177 (25 mg) as a starting material, the compound shown in Table 6 (5.0 mg) was obtained in the same manner as that of Example 214.

Example 216

[0743] By using the compound obtained in Example 180 (50 mg) as a starting material, the compound shown in Table 6 (35.6 mg) was obtained in the same manner as that of Example 214.

Example 217

[0744] 

(1) By using the compound obtained in Example 1 (1.58 g) and the compound obtained in Reference Example 15 (1.36 g) as starting materials, a biaryl compound (0.81 g) was obtained in the same manners as those of Example 7, (1), (2), (3) and Example 23, (2).

(2) By using the compound obtained in (1) mentioned above (0.8 g) as a starting material, the compound shown in Table 6 (154 mg) was obtained in the same manners as those of Example 126, (1), Example 176 and Example 214.

Example 218

[0745] The compound obtained in Example 176, (4) (100 mg) was dissolved in 1 N hydrochloric acid (2 ml) and ethanol (1 ml), and the solution was stirred at 50°C for 5 hours. The reaction mixture was neutralized with 1 N aqueous sodium hydroxide, and then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1). By using the resulting compound (50 mg) as a starting material, the compound shown in Table 6 (12.4 mg) was obtained in the same manners as those of Example 112, (2) and Example 214.

Example 219

[0746] 

(1) By using the compound obtained in Example 70, (1) (606 mg) as a starting material, a 4"-hydroxy compound (401 mg) was obtained in the same manner as that of Example 126, (1).

[0747] 

(2) The compound obtained in (1) mentioned above (394 mg) was dissolved in chloroform (5 ml), the solution was added pyridine (5 ml), 4-dimethylaminopyridine (93.2 mg) and acetic anhydride (108 µl) under ice cooling, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone=8:1). The purified compound (372 mg) was dissolved in pyridine (7 ml) again, the solution was added with 4-dimethylaminopyridine (93.2 mg) and acetic anhydride (0.32 ml) under ice cooling, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone=8:1) to obtain a 4"-O-acetyl compound (336 mg).

[0748] 

(3) By using the compound obtained in (2) mentioned above (323 mg) as a starting material, a 9-oxime compound was obtained in the same manners as those of Example 7, (4), Example 176, (3), (4), Example 125, (3) and Example 214.

[0749] 

(4) The compound obtained in (3) mentioned above (22.0 mg) was dissolved in methanol (1.5 ml) and tetrahydrofuran (0.5 ml), the solution was added with sodium methoxide (6.92 mg) under ice cooling, and the mixture was stirred at 50°C for 6 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 6 (14.0 mg).

Example 220

[0750] By using the compound obtained in Example 17, (2) (70 mg) as a starting material, the compound shown in Table 6 (0.84 mg) was obtained in the same manner as that of Example 219 (Example 126, (1), Example 219, (2), Example 7, (4), Example 176, (3), (4), Example 125, (3), Example 214 and Example 219, (4)).

Example 221

[0751] 

(1) By using the compound obtained in Example 1 (3.0 g) and 2-[3-(benzyloxy)propyl]oxirane (3.48 g) obtained by the method described in the literature (European Journal of Organic Chemistry, 2000, p.1219) as starting materials, a cyclized compound (401 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (114 mg) as a starting material, the compound shown in Table 6 (14.6 mg) was obtained in the same manner as that of Example 219 (Example 126, (1), Example 219, (2), Example 7, (4), Example 176, (3), (4), Example 125, (3), Example 214 and Example 219, (4)).

Example 222

[0752] The compound obtained in Example 221 (14.6 mg) as a starting material, the compound shown in Table 6 (3.7 mg) was obtained in the same manner as that of Example 73.

Example 223

[0753] 

(1) By using the compound obtained in Example 176, (4) (381 mg) as a starting material, a 9-oxime compound (299 mg) was obtained in the same manner as that of Example 214.

(2) The compound obtained in (1) mentioned above (217 mg) was dissolved in tetrahydrofuran (5 ml), the solution was added with allyl bromide (33 µl) and potassium hydroxide (70.1 mg), and the mixture was stirred at room temperature for 18 hours. The mixture was further added with allyl bromide (7 µl) and potassium hydroxide (14.1 mg), and the mixture was stirred at room temperature for 18 hours. The mixture was further added with allyl bromide (7 µl) and potassium hydroxide (14.1 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone = 8:1) to obtain the compound shown in Table 6 (80 mg).

Example 224

[0754] The compound obtained in Example 214 (48.4 mg) was dissolved in tetrahydrofuran (3 ml), the solution was added with 2-bromoethylamine hydrobromide (40.6 mg), potassium hydroxide (37.1 mg) and 18-crown-6-ether (175 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated brine and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) and silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0 to 10:1:0.1) to obtain the compound shown in Table 6 (34.1 mg).

Example 225

[0755] By using the compound obtained in Example 214 (50.8 mg) and benzyl 2-bromoethyl ether (44.8 mg) as starting materials, the compound shown in Table 6 (22.7 mg) was obtained in the same manner as that of Example 224.

Example 226

[0756] By using the compound obtained in Example 225 (5.6 mg) as a starting material, the compound shown in Table 6 (4.7 mg) was obtained in the same manner as that of Example 43.

Example 227

[0757] By using the compound obtained in Example 224 (8.4 mg) as a starting material, the compound shown in Table 6 (5.9 mg) was obtained in the same manner as that of Example 7, (2).

Example 228

[0758] By using the compound obtained in Example 214 (78.7 mg) and benzyl bromoacetate (74.0 mg) as starting materials, the compound shown in Table 6 (5.8 mg) was obtained in the same manner as that of Example 224.

Example 229

[0759] By using the compound obtained in Example 214 (18.6 mg) and 3-bromopropylamine hydrobromide (16.7 mg) as starting materials, the compound shown in Table 6 (10.2 mg) was obtained in the same manner as that of Example 224.

Example 230

[0760] By using the compound obtained in Example 214 (78.7 mg) and benzyl bromoacetate (74.0 mg) as starting materials, the compound shown in Table 6 (25.4 mg) was obtained in the same manner as that of Example 224.

Example 231

[0761] The compound obtained in Example 230 (12.1 mg) was dissolved in chloroform, the solution was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (14.7 mg) and 4-(3-aminopropyl)-quinoline (14.3 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 2005-200318) under ice cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with chloroform and saturated brine, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0 to 10:1:0.1) and preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 6 (1.7 mg).

Example 232

[0762] By using the compound obtained in Example 224 (16.8 mg) and phthalimide acetaldehyde (4.5 mg) as starting materials, the compound shown in Table 6 (12.0 mg) was obtained in the same manner as that of Example 7, (2).

Example 233

[0763] By using the compound obtained in Example 224 (16.8 mg) and phthalimide acetaldehyde (4.5 mg) as starting materials, the compound shown in Table 6 (1.7 mg) was obtained in the same manner as that of Example 7, (2).

Example 234

[0764] The compound obtained in Example 232 (12.0 mg) was dissolved in ethanol (1 ml), the solution was added with hydrazine monohydrate (0.64 mg) under ice cooling, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 6 (5.4 mg).

Example 235

[0765] 

(1) By using the compound obtained in Example 224 (8.4 mg) as a starting material, a diacetyl compound (7.7 mg) was obtained in the same manner as that of Example 176, (3).

(2) The compound obtained in (1) mentioned above (6.9 mg) was dissolved in methanol (1 ml), and the solution was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 6 (3.2 mg).

Syntheses of Examples 236 to 239

[0766] Preparation methods of compounds represented by the formula (N) having R defined in Table 7 are shown below.

[Table 7]

[0767] 

Table 7

Example	R	ESI MS (M+H)	1H-NMR CDCl3, δ (ppm)
236		882.8	(500 MHz) : 0.85 (t, J=7.26 Hz, 3 H) 0.88 - 1.31 (m, 25 H) 1.45 - 1.65 (m, 5 H) 1.87 - 1.97 (m, 1 H) 1.97 - 2.15 (m, 1 H) 2.08 (s, 3 H) 2.20 - 2.45 (m, 2 H) 2.24 (s, 6 H) 2.46 - 2.63 (m, 3 H) 2.68 - 2.79 (m, 1 H) 2.89 - 2.96 (m, 1 H) 2.97 - 3.05 (m, 1 H) 3.32 (s, 11 H) 3.91 - 4.04 (m, 1 H) 4.09 - 4.20 (m, 2 H) 4.49 (d, J=6.88 Hz, 1 H) 4.72 - 4.85 (m, 2 H) 5.02 (d, J=13.00 Hz, 1 H) 5.16 (d, J=13.00 Hz, 1 H) 6.76 (br. s., 1 H) 7.20 - 7.44 (m, 5 H)
237		839.7	(600 MHz) : 0.86 (t, J=7.34 Hz, 3 H) 0.97 - 1.29 (m, 25 H) 1.47 - 1.69 (m, 5 H) 1.87 - 1.99 (m, 1 H) 2.07 - 2.20 (m, 1 H) 2.12 (s, 3 H) 2.22 - 2.62 (m, 6 H) 2.29 (s, 6 H) 2.71 - 2.82 (m, 1 H) 2.94 - 3.05 (m, 2 H) 3.26 - 3.68 (m, 6 H) 3.33 (s, 3 H) 3.94 - 4.18 (m, 3 H) 4.48 - 4.58 (m, 3 H) 4.75 - 4.87 (m, 2 H) 7.21 - 7.36 (m, 5 H)
238		748.7	(600 MHz) : 0.80 - 1.34 (m, 28 H) 1.50 - 1.70 (m, 5 H) 1.84 - 2.21 (m, 2 H) 2.16 (s, 3 H) 2.24 - 2.64 (m, 7 H) 2.29 (s, 6 H) 2.72 - 3.08 (m, 4 H) 3.18 - 3.60 (m, 4 H) 3.34 (s, 3 H) 3.78 - 4.16 (m, 4 H) 4.50 - 4.59 (m, 1 H) 4.74 - 4.86 (m, 2 H)
239		749.7	(600 MHz) : 0.86 (t, J=7.57 Hz, 3 H) 0.94 - 1.36 (m, 25 H) 1.47 - 1.67 (m, 5 H) 1.87 - 1.96 (m, 1 H) 2.04 - 2.17 (m, 1 H) 2.09 (s, 3 H) 2.23 - 2.41 (m, 8 H) 2.47 - 2.63 (m, 3 H) 2.69 - 2.78 (m, 1 H) 2.91 - 2.97 (m, 1 H) 3.00 - 3.07 (m, 1 H) 3.24 - 3.39 (m, 1 H) 3.34 (s, 3 H) 3.43 - 3.67 (m, 5 H) 3.79 - 3.86 (m, 1 H) 3.95 - 4.04 (m, 1 H) 4.10 - 4.41 (m, 3 H) 4.56 (d, J=6.88 Hz, 1 H) 4.74 - 4.85 (m, 2 H)

Example 236

[0768] By using the compound obtained in Example 4 (225 mg) as a starting material, the compound shown in Table 7 (16 mg) was obtained in the same manner as that of Example 7.

Example 237

[0769] By using the compound obtained in Example 5 (180 mg) as a starting material, the compound shown in Table 7 (16 mg) was obtained in the same manner as that of Example 7.

Example 238

[0770] The compound obtained in Example 236 (24 mg) was dissolved in methanol (0.3 ml), the solution was added with 5% palladium-carbon (4 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form, acetone:hexane:triethylamine = 10:40:0.2) to obtain the compound shown in Table 7 (8.7 mg).

Example 239

[0771] The compound obtained in Example 237 (11 mg) was dissolved in methanol (0.1 ml), the solution was added with 20% palladium hydroxide-carbon (2 mg), and the mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (0.1 ml), the solution was added with 20% palladium hydroxide-carbon (2 mg), and the mixture was stirred at room temperature for 17 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (0.1 ml), the solution was added with 20% palladium hydroxide-carbon (2 mg), and the mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 7 (1.7 mg).

Syntheses of Examples 240 to 243

[0772] Preparation methods of compounds represented by the formula (O) having R¹⁰, and R²⁰ defined in Table 8 are shown below.

[Table 8]

[0773] 

Table 8

Example	R10	R20	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
240	H		675.3	(500 MHz) : 0.93 (d, J=6.88 Hz, 3 H) 1.01 (d, J=6.88 Hz, 3 H) 1.07 (d, J=7.65 Hz, 3 H) 1.11 (d, J=7.65 Hz, 3 H) 1.21 (d, J=6.12 Hz, 3 H) 1.21 - 1.31 (m, 1 H) 1.23 (s, 3 H) 1.27 (d, J=6.12 Hz, 3 H) 1.30 (s, 3 H) 1.53 (dd, J=15.29, 4.59 Hz, 1 H) 1.61 - 1.73 (m, 2 H) 1.80 (t, J=12.61 Hz, 1 H) 1.98 - 2.08 (m, 1 H) 2.10 - 2.16 (m, 2 H) 2.30 (s, 6 H) 2.34 - 2.40 (m, 1 H) 2.37 (s, 3 H) 2.42 - 2.53 (m, 1 H) 2.60 (q, J=6.88 Hz, 1 H) 2.67 - 2.76 (m, 1 H) 2.77 - 2.86 (m, 1 H) 2.99 (t, J=9.94 Hz, 1 H) 3.06 - 3.15 (m, 1 H) 3.19 - 3.26 (m, 1 H) 3.34 (s, 3 H) 3.44 - 3.52 (m, 1 H) 3.63 (d, J=8.41 Hz, 1 H) 3.76 (t, J=11.09 Hz, 1 H) 3.96 - 4.04 (m, 1 H) 4.05 - 4.08 (m, 1 H) 4.41 (d, J=6.88 Hz, 1 H) 4.47 (d, J=11.47 Hz, 1 H) 4.72 (d, J=4.59 Hz, 1 H)
241	H		690.3	(300 MHz) : 0.98 - 1.12 (m, 9 H) 1.20 (d, J=7.15 Hz, 3 H) 1.21 - 1.32 (m, 1 H) 1.22 - 1.25 (m, 3 H) 1.23 (s, 3 H) 1.30 (d, J=6.22 Hz, 3 H) 1.37 (s, 3 H) 1.48 - 2.06 (m, 5 H) 2.26 (s, 3 H) 2.30 (s, 6 H) 2.31 - 2.53 (m, 2 H) 2.64 - 2.83 (m, 2 H) 2.84 - 2.95 (m, 1 H) 2.96 - 3.06 (m, 1 H) 3.27 (dd, J=10.26, 7.31 Hz, 1 H) 3.31 (s, 3 H) 3.42 - 3.58 (m, 3 H) 3.74 - 3.89 (m, 1 H) 3.95 - 4.13 (m, 2 H) 4.27 - 4.39 (m, 2 H) 4.43 (d, J=7.31 Hz, 1 H) 4.77 (d, J=4.51 Hz, 1 H)
242	Et		718.6	(500 MHz) : 0.88 (t, J=7.55 Hz, 3 H) 0.99 - 1.37 (m, 25 H) 1.48 - 1.68 (m, 5 H) 1.90 - 1.96 (m, 1 H) 2.08 - 2.37 (m, 3 H) 2.18 (s, 3 H) 2.28 (s, 6 H) 2.40 - 2.49 (m, 1 H) 2.53 - 2.77 (m, 3 H) 2.95 - 3.03 (m, 1 H) 3.21 - 3.69 (m, 5 H) 3.30 (s, 3 H) 3.73 - 3.84 (m, 1 H) 3.94 - 4.03 (m, 1 H) 4.05 - 4.13 (m, 1 H) 4.42 (d, J=7.20 Hz, 1 H) 4.76 - 4.81 (m, 1 H) 5.00 - 5.08 (m, 1 H) 5.15 (br. s., 1 H)
243	Et		761.6	(600 MHz) : 0.88 (t, J=7.57 Hz, 3 H) 0.91 - 1.40 (m, 25 H) 1.47 - 1.58 (m, 3 H) 1.60 - 1.68 (m, 1 H) 1.89 - 1.98 (m, 2 H) 2.08 - 2.37 (m, 3 H) 2.21 (s, 3 H) 2.28 (s, 6 H) 2.41 - 2.48 (m, 1 H) 2.52 - 2.58 (m, 1 H) 2.66 - 2.82 (m, 4 H) 2.85 - 3.03 (m, 3 H) 3.20 - 3.52 (m, 4 H) 3.30 (s, 3 H) 3.63 (s, 1 H) 3.77 - 3.86 (m, 1 H) 3.95 - 4.11 (m, 3 H) 4.42 (d, J=7.34 Hz, 1 H) 4.76 - 4.82 (m, 1 H) 5.01 - 5.10 (m, 1 H)

Example 240

[0774] 

(1) The compound obtained in Example 2 (30 g) was dissolved in toluene (700 ml), the solution was added with triethylamine (51 ml) and 2-bromoethyl alcohol (22 ml), and the mixture was stirred at 80°C for 4 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0.1) to obtain a 10a-N-(2-hydroxyethyl) compound (19.4 g).

(2) By using the compound obtained in (1) mentioned above (19.4 g) as a starting material, a cyclized compound (3.0 g) was obtained in the same manners as those of Example 7, (2) and (3).

(3) By using the compound obtained in (2) mentioned above (0.67 g) as a starting material, a 4"-hydroxy compound (0.52 g) was obtained in the same manner as that of Example 126, (1).

[0775] 

(4) The compound obtained in (3) mentioned above (0.5 g) was dissolved in tetrahydrofuran (5 ml), the solution was added with potassium carbonate (0.3 g) and N,N'-carbonyldiimidazole (0.27 g), the mixture was stirred at room temperature for 80 minutes, and then further added with potassium carbonate (0.3 g) and N,N'-carbonyldiimidazole (0.27 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was diluted with ethyl acetate, and washed successively with saturated aqueous ammonium chloride and saturated brine. Then, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (5 ml). The solution was added with a solution of sodium hydride (29 mg) and benzyl alcohol (0.11 ml) in tetrahydrofuran (5 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a 4"-O-benzyloxycarbonyl compound (0.35 g).

[0776] 

(5) By using the compound obtained in (4) mentioned above (0.35 g) as a starting material, a 2'-acetyl compound (105 mg) was obtained in the same manners as those of Example 7, (4) and Example 176, (3).

(6) By using the compound obtained in (5) mentioned above (50 mg) as a starting material, the compound shown in Table 8 (17 mg) was obtained in the same manners as those of Example 176, (4) and (5).

Example 241

[0777] The compound obtained in Example 240 (23 mg) was dissolved in methanol (1 ml), the solution was added with 50% aqueous hydroxyamine (30 µl) and acetic acid (15 µl), and the mixture was stirred at 50°C for 40 hours. The reaction mixture was added with ethyl acetate and 0.5 N aqueous sodium hydroxide, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 9:1:0.1) to obtain the compound shown in Table 8 (6.5 mg).

Example 242

[0778] 

(1) By using the compound obtained in Example 206, (3) (100 mg) as a starting material, a 9-oxime compound (56 mg) was obtained in the same manner as that of Example 214.

(2) By using the compound obtained in (1) mentioned above (20 mg) as a starting material, the compound shown in Table 8 (7 mg) was obtained in the same manner as that of Example 7, (4).

Example 243

[0779] 

(1) By using the compound obtained in Example 242, (1) (29 mg) as a starting material, an aminoethyl compound (14 mg) was obtained in the same manner as that of Example 224.

(2) By using the compound obtained in (1) mentioned above (14 mg) as a starting material, the compound shown in Table 8 (8 mg) was obtained in the same manner as that of Example 7, (4).

Syntheses of Examples 244 to 247

[0780] Preparation methods of compounds represented by the formula (P) having R defined in Table 9 are shown below.

[Table 9]

[0781] 

Table 9

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
244	H	705.4
245	Et	733.4	(600 MHz) : 0.76 - 0.83 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 0.97 (t, J=7.79 Hz, 2 H) 0.99 - 1.36 (m, 4 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.79 Hz, 3 H) 1.22 (d, J=7.79 Hz, 3 H) 1.22 (s, 3 H) 1.29 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 2 H) 1.69 - 1.77 (m, 1 H) 1.77 - 1.87 (m, 1 H) 2.21 - 2.40 (m, 12 H) 2.46 - 2.58 (m, 1 H) 2.59 - 2.70 (m, 1 H) 2.77 - 2.86 (m, 1 H) 2.91 (d, J=14.67 Hz, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.14 - 3.25 (m, 1 H) 3.15 - 3.25 (m, 3 H) 3.32 (s, 3 H) 3.38 - 3.50 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.02 - 4.09 (m, 1 H) 4.15 - 4.22 (m, 1 H) 4.37 (d, J=7.34 Hz, 1 H) 4.50 - 4.62 (m, 1 H) 4.95 (d, J=4.13 Hz, 1 H)
246		745.4	(600 MHz) : 0.66 (t, J=8.02 Hz, 3 H) 0.75 - 0.82 (m, 6 H) 0.89 - 0.96 (m, 5 H) 1.09 (d, J=7.34 Hz, 3 H) 1.14 - 1.17 (m, 3 H) 1.17 - 1.24 (m, 5 H) 1.28 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=14.90, 4.81 Hz, 1 H) 1.60 - 1.87 (m, 2 H) 2.19 - 2.40 (m, 10 H) 2.45 - 2.66 (m, 2 H) 2.78 - 2.85 (m, 1 H) 2.93 (d, J=15.13 Hz, 1 H) 3.00 (t, J=9.17 Hz, 1 H) 3.21 (s, 3 H)3.13 - 3.26 (m, 1 H) 3.32(s, 3 H) 3.29 - 3.33 (m, 2 H) 3.40 - 3.51 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.15 - 4.21 (m, 1 H) 4.37 (d, J=7.34 Hz, 1 H) 4.55 - 4.66 (m, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 5.10 (m, 2 H) 5.78 - 5.88 (m, 1 H)
247		795.4	(600 MHz) : 0.53 - 0.69 (m, 3 H) 0.78 - 0.83 (m, 3 H) 0.84 - 0.90 (m, 3 H) 0.91 - 0.99 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.18 (d, J=7.34 Hz, 3 H) 1.19 - 1.25 (m, 8 H) 1.29 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.36, 4.81 Hz, 1 H) 1.64 (d, J=11.46 Hz, 1 H) 1.75 - 1.92 (m, 1 H) 2.16 - 2.32 (m, 9 H) 2.36 (d, J=15.13 Hz, 1 H) 2.42 - 2.51 (m, 2 H) 2.81 - 2.88 (m, 1 H) 2.98 - 3.04 (m, 2 H) 3.16 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.41 - 3.49 (m, 1 H) 3.51 - 3.59 (m, 1 H) 3.65 (d, J=13.76 Hz, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.76 (d, J=14.21 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.17 - 4.22 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.61 - 4.70 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 7.22 (t, J=7.34 Hz, 1 H) 7.30 (t, J=7.57 Hz, 2 H) 7.35 (d, 2 H)

Example 244

[0782] 

(1) The compound obtained in Example 1 (1.0 g) was dissolved in chloroform (5 ml), the solution was added with benzaldehyde (107 mg) and sodium triacetoxyborohydride (322 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain a 10a-N-benzyl compound (717 mg).

[0783] 

(2) By using the compound obtained in (1) mentioned above (710 mg) as a starting material, a cyclized compound (35 mg) was obtained in the same manners as those of Example 7, (1) and (3).

[0784] 

(3) By using the compound obtained in (2) mentioned above (30 mg) as a starting material, the compound shown in Table 9 (1.7 mg) was obtained in the same manners as those of Example 7, (4) and Example 73.

Example 245

[0785] 

(1) By using the compound obtained in Example 1 (5.03 g) and (S)-1,2-epoxybutane as starting materials, an adduct compound (2.39 g) was obtained in the same manner as that of Example 7, (1).

[0786] 

(2) The compound obtained in (1) mentioned above (2.39 g) and triphenylphosphine (2.36 g) were dissolved in tetrahydrofuran (36 ml), the solution was added with a 40% solution of diisopropyl azodicarboxylate in toluene (4.7 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was added with distilled water and chloroform. The layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine =90:5:0.1 to 45:5:0.1) to obtain a cyclized compound (0.63 g).

[0787] 

(3) By using the compound obtained in (2) mentioned above (50 mg) and acetaldehyde as starting materials, an ethyl compound (24 mg) was obtained in the same manner as that of Example 7, (2).

[0788] 

(4) By using the compound obtained in (3) mentioned above (24 mg) as a starting material, the compound shown in Table 9 (10 mg) was obtained in the same manner as that of Example 7, (4).

Example 246

[0789] 

(1) The compound obtained in Example 245, (2) (70 mg) was dissolved in dimethylformamide (1 ml), the solution was added with allyl bromide (116 mg) and potassium carbonate (186 mg), and the mixture was stirred at room temperature for 21 hours. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1) to obtain an allyl compound (21 mg).

(2) By using the compound obtained in (1) mentioned above (21 mg) as a starting material, the compound shown in Table 9 (5 mg) was obtained in the same manner as that of Example 7, (4).

Example 247

[0790] By using the compound obtained in Example 245, (2) (48 mg) and benzyl bromide as starting materials, the compound shown in Table 9 (5 mg) was obtained in the same manners as those of Example 246, (1) and Example 7, (4).

Example 248: Synthesis of the compound represented by the formula (Q)

[0791] 

[0792] 

(1) By using the compound obtained in Example 1 (4.5 g) and benzyl (S)-(+)-glycidyl ether (3.0 g) as starting materials, an adduct compound (2.74 g) was obtained in the same manner as that of Example 7, (1).

[0793] 

(2) The compound obtained in (1) mentioned above (2.0 g) was dissolved in tetrahydrofuran (300 ml), the solution was added with a 2.2 M solution of diethyl azodicarboxylate in toluene (1.57 ml) and triphenylphosphine (0.91 g), and the mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a cyclized compound (0.3 g).

[0794] 

(3) The compound obtained in (2) mentioned above (0.14 g) was dissolved in tetrahydrofuran (10 ml), the solution was added with 20% palladium hydroxide-carbon (0.5 g), and the mixture was stirred at room temperature for 8 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue (65 mg) was dissolved in chloroform (3 ml) and pyridine (0.05 ml), the solution was added dropwise with a solution of triphosgene (18 mg) in chloroform (1 ml) by small and small, and then the mixture was stirred at room temperature for 5 hours. The reaction mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a carbamate compound (18 mg).

[0795] 

(4) By using the compound obtained in (3) mentioned above (18 mg) as a starting material, the title compound (11.6 mg) was obtained in the same manner as that of Example 7, (4).
MS (ESI) m/z = 733.3 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm):1.06 (d, J=7.34Hz, 3H), 1.12 (d, J=7.34Hz, 3H), 1.13-1.32 (m, 2H), 1.19 (d, J=6.88Hz, 3H), 1.22 (d, J=5.96Hz, 3H), 1.24-1.25 (m, 6H), 1.36 (d, J=6.42Hz, 3H), 1.44 (d, J=6.88Hz, 3H), 1.58 (dd, J=15.36, 4.81Hz, 1H), 1.60-1.65 (m, 1H), 1.88-2.05 (m, 2H), 2.07-2.13 (m, 1H), 2.28 (s, 1H), 2.28 (s, 6H), 2.36 (d, J=15.13Hz, 1H), 2.43-2.52 (m, 1H), 2.68-2.77 (m, 1H), 3.09 (t, J=9.17Hz, 1H), 3.20-3.27 (m, 1H), 3.32-3.40 (m, 2H), 3.34 (s, 3H), 3.36 (s, 3H), 3.41-3.48 (m, 1H), 3.50-3.59 (m, 1H), 3.72 (d, J=3.67Hz, 1H), 3.74 (d, J=5.50Hz, 1H), 3.98-4.05 (m, 1H), 4.13-4.20 (m, 1H), 4.23 (d, J=11.92Hz, 1H), 4.40-4.49 (m, 1H), 4.51-4.59 (m, 2H), 4.97-5.04 (m, 1H)

Example 249: Synthesis of the compound represented by the formula (R)

[0796] 

[0797] 

(1) By using the compound obtained in Example 1 (3.0 g) and (R)-1,2-epoxypropane benzyl ether (2.0 g) as starting materials, an adduct compound (1.13 g) was obtained in the same manner as that of Example 7, (1).

[0798] 

(2) The compound obtained in (1) mentioned above (0.6 g) was dissolved in tetrahydrofuran (90 ml), the solution was added with a 1.9 M solution of diisopropyl azodicarboxylate in toluene (0.55 ml) and triphenylphosphine (0.27 g), and the mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a cyclized compound (0.42 g).

[0799] 

(3) By using the compound obtained in (2) mentioned above (59 mg) as a starting material, the title compound (5.7 mg) was obtained in the same manners as those of Example 248, (3) and Example 7, (4).
MS (ESI) m/z = 575.2 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm):1.10 (d, J=6.88Hz, 3H), 1.15-1.19 (m, 3H), 1.21-1.30 (m, 13H), 1.32 (s, 3H), 1.40 (dd, J=15.36, 6.19Hz, 1H), 1.61-1.67 (m, 1H), 1.72-1.80 (m, 1H), 1.84-1.92 (m, 1H), 2.00-2.07 (m, 1H), 2.24 (s, 6H), 2.44-2.50 (m, 1H), 2.70-2.77 (m, 1H), 3.15 (s, 3H), 3.23 (dd, J=10.32, 7.57Hz, 1H), 3.26-3.29 (m, 1H), 3.48-3.54 (m, 1H), 3.57-3.64 (m, 1H), 3.82-3.85 (m, 1H), 3.89-4.02 (m, 1H), 4.03-4.14 (m, 1H), 4.18-4.23 (m, 1H), 4.28-4.34 (m, 1H), 4.47 (d, J=7.34Hz, 1H), 4.63-4.70 (m, 1H), 5.00-5.04 (m, 1H)

Syntheses of Examples 250 to 258

[0800] Preparation methods of compounds represented by the formula (S) having R^1S, R^2S and R^3S defined in Table 10 are shown below.

[Table 10-1]

[0801] 

Table 10

Example	X	R1S	R2S	R3S	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
250		cladinosyl	H	H	743.7	(300 MHz) : 0.83 - 0.93 (m, 9 H) 1.04 - 1.32 (m, 2 H) 1.13 (d, J=7.31 Hz, 3 H) 1.17 (d, J=7.31 Hz, 3 H) 1.23 (d, J=6.22 Hz, 3 H) 1.23 (s, 3 H) 1.29 (d, J=6.22 Hz, 3 H) 1.38 (s, 3 H) 1.49 - 1.79 (m, 4 H) 1.91 - 2.53 (m, 9 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.70 - 3.08 (m, 3 H) 3.17 - 3.27 (m, 1 H) 3.34 (s, 3 H) 3.44 - 3.59 (m, 2 H) 3.66 (d, J=8.24 Hz, 1 H) 3.99 - 4.10 (m, 1 H) 4.14 - 4.24 (m, 2 H) 4.30 - 4.33 (m, 1 H) 4.41 (d, J=7.31 Hz, 1 H) 4.64 - 4.74 (m, 1 H) 4.96 (d, J=4.97 Hz, 1 H)
251		cladinosyl	H		871.7	(300 MHz) : 0.83 (t, J=7.38 Hz, 3 H) 0.88 (d, J=7.31 Hz, 3 H) 0.91 (d, J=6.84 Hz, 3 H) 1.10 - 1.37 (m, 2 H) 1.16 (d, J=7.31 Hz, 3 H) 1.19 (d, J=7.46 Hz, 3 H) 1.25 (s, 3 H) 1.27 (d, J=6.22 Hz, 3 H) 1.34 (d, J=6.37 Hz, 3 H) 1.44 - 2.10 (m, 5 H) 1.47 (s, 3 H) 2.23 - 2.55 (m, 7 H) 2.30 (s, 6 H) 2.31 (s, 3 H) 2.74 - 2.96 (m, 2 H) 3.05 (t, J=9.25 Hz, 1 H) 3.20 - 3.28 (m, 1 H) 3.35 (s, 3 H) 3.46 - 3.60 (m, 2 H) 3.75 (d, J=8.08 Hz, 1 H) 4.03 - 4.15 (m, 1 H) 4.30 (d, J=2.64 Hz, 1 H) 4.41 - 4.71 (m, 4 H) 5.07 (d, J=4.35 Hz, 1 H) 7.63 (dd, J=8.55, 4.20 Hz, 1 H) 8.36 - 8.41 (m, 1 H) 8.45 - 8.48 (m, 1 H) 8.98 - 9.01 (m, 2 H)
252		cladinosyl	H		888.7	(300 MHz) : 0.84 - 0.94 (m, 9 H) 1.09 - 1.35 (m, 8 H) 1.15 (d, J=7.31 Hz, 3 H) 1.19 (d, J=7.46 Hz, 3 H) 1.32 (d, J=6.22 Hz, 3 H) 1.44 (s, 3 H) 1.49 - 1.88 (m, 4 H) 1.95 - 2.54 (m, 8 H) 2.29 (s, 6 H) 2.34 (s, 3 H) 2.73 - 2.98 (m, 2 H) 3.04 (t, J=9.17 Hz, 1 H) 3.23 (dd, J=10.65, 7.38 Hz, 1 H) 3.34 (s, 3 H) 3.45 - 3.56 (m, 2 H) 3.70 (d, J=8.39 Hz, 1 H) 4.01 - 4.11 (m, 1 H) 4.21 - 4.24 (m, 1 H) 4.43 (d, J=7.15 Hz, 1 H) 4.46 - 4.74 (m, 3 H) 5.00 (d, J=3.89 Hz, 1 H) 7.30 (s, 1 H) 7.61 (dd, J=8.55, 4.97 Hz, 1 H) 8.26 (dd, J=8.55, 1.71 Hz, 1 H) 9.25 (dd, J=4.97, 1.71 Hz, 1 H)

[0802] 

[Table 10-2]

253		cladinosyl	H	H	755.6	(300 MHz) : 0.93 (t, J=7.54 Hz, 3 H) 1.09 (d, J=7.46 Hz, 3 H) 1.07 - 1.33 (m, 14 H) 1.13 (d, J=6.53 Hz, 3 H) 1.19 (d, J=7.15 Hz, 3 H) 1.30 (d, J=6.22 Hz, 3 H) 1.45 - 1.83 (m, 6 H) 2.07 - 2.51 (m, 5 H) 2.28 (s, 6 H) 2.67 - 2.79 (m, 1 H) 2.98 - 3.10 (m, 2 H) 3.17 (dd, J=10.26, 7.31 Hz, 1 H) 3.31 (s, 3 H) 3.45 (dd, 1 H) 3.58 (dd, J=10.57, 3.11 Hz, 1 H) 3.64 (d, J=7.62 Hz, 1 H) 3.74 - 3.80 (m, 1 H) 3.81 - 3.90 (m, 1 H) 3.93 - 4.05 (m, 2 H) 4.21 (ddd, J=21.18, 16.44, 2.49 Hz, 2 H) 4.37 (d, J=7.30 Hz, 1 H) 4.85 - 4.98 (m, 2 H)
254		cladinosyl	H		883.7	(300 MHz) : 0.91 (t, J=7.62 Hz, 3 H) 1.09 - 1.32 (m, 11 H) 1.13 (d, J=7.62 Hz, 3 H) 1.17 (d, J=6.53 Hz, 3 H) 1.21 (d, J=7.15 Hz, 3 H) 1.24 (s, 3 H) 1.30 (d, J=6.53 Hz, 3 H) 1.51 - 1.88 (m, 7 H) 2.20 - 2.48 (m, 3 H) 2.28 (s, 6 H) 2.72 - 2.81 (m, 1 H) 2.98 - 3.11 (m, 2 H) 3.19 (dd, J=10.26, 7.31 Hz, 1 H) 3.32 (s, 3 H) 3.41 - 3.56 (m, 1 H) 3.60 - 3.90 (m, 4 H) 3.97 - 4.05 (m, 2 H) 4.40 (d, J=7.15 Hz, 1 H) 4.46 - 4.61 (m, 2 H) 4.91 (d, J=4.20 Hz, 1 H) 4.94 - 5.03 (m, 1 H) 7.61 (dd, J=8.55, 4.20 Hz, 1 H) 8.35 - 8.40 (m, 1 H) 8.45 - 8.47 (m, 1 H) 8.97 - 9.01 (m, 2 H)
255		cladinosyl	H		900.7	(300 MHz) : 0.93 (t, J=7.54 Hz, 3 H) 1.12 (d, J=7.46 Hz, 3 H) 1.10 - 1.34 (m, 14 H) 1.15 (d, J=6.37 Hz, 3 H) 1.21 (d, J=7.15 Hz, 3 H) 1.31 (d, J=6.22 Hz, 3 H) 1.54 - 1.85 (m, 6 H) 2.19 - 2.30 (m, 3 H) 2.32 (s, 6 H) 2.43 - 2.55 (m, 1 H) 2.70 - 2.80 (m, 1 H) 2.98 - 3.25 (m, 3 H) 3.32 (s, 3 H) 3.45 - 3.56 (m, 1 H) 3.62 (dd, J=10.10, 2.80 Hz, 1 H) 3.71 (d, J=7.31 Hz, 1 H) 3.74 - 3.83 (m, 2 H) 3.96 (d, J=8.55 Hz, 1 H) 3.96 - 4.06 (m, 2 H) 4.41 (d, J=7.15 Hz, 1 H) 4.47 - 4.61 (m, 2 H) 4.90 (d, J=4.35 Hz, 1 H) 4.93 - 5.05 (m, 1 H) 7.31 (s, 1 H) 7.61 (dd, J=8.55, 4.97 Hz, 1 H) 8.25 (dd, J=8.55, 1.71 Hz, 1 H) 9.24 (dd, J=4.97, 1.71 Hz, 1 H)
256					740.4	(300 MHz) : 0.95 (t, J=7.46 Hz, 3 H) 1.12 - 1.77 (m, 12 H) 1.19 (d, J=6.53 Hz, 3 H) 1.26 (d, J=6.06 Hz, 3 H) 1.41 (d, J=6.84 Hz, 3 H) 1.59 (s, 3 H) 2.08 - 2.19 (m, 1 H) 2.28 (s, 6 H) 2.41 - 2.53 (m, 1 H) 2.86 - 2.99 (m, 1 H) 3.10 (dd, J=15.08, 10.41 Hz, 1 H) 3.20 (dd, J=10.26, 7.31 Hz, 1 H) 3.46 - 3.75 (m, 4 H) 3.82 (d, J=13.37 Hz, 1 H) 3.96 - 4.16 (m, 2 H) 4.13 (d, J=11.04 Hz, 1 H) 4.22 (d, J=9.48 Hz, 1 H) 4.33 (d, J=7.31 Hz, 1 H) 4.81 - 4.93 (m, 1 H) 7.30 (s, 1 H) 7.60 (dd, J=8.63, 5.05 Hz, 1 H) 8.25 (dd, J=8.55, 1.71 Hz, 1 H) 9.24 (dd, J=5.13, 1.71 Hz. 1 H)

[0803] 

[Table 10-3]

257		cladinosyl	H		901.5	(300 MHz) : 0.89 (t, J=7.46 Hz, 3 H) 1.05 (d, J=6.68 Hz, 3 H) 1.12 (d, J=7.62 Hz, 3 H) 1.17 (d, J=7.15 Hz, 3 H) 1.20 (d, J=6.84 Hz, 3 H) 1.29 (s, 7 H) 1.30 (d, J=6.06 Hz, 3 H) 1.40 (s, 3 H) 1.53 - 1.70 (m, 4 H) 1.80 - 1.85 (m, 2 H) 1.94 - 1.99 (m, 1 H) 2.01 (s, 3 H) 2.13 (d, J=10.41 Hz, 1 H) 2.30 (s, 6 H) 2.37 - 2.43 (m, 1 H) 2.43 - 2.55 (m, 1 H) 2.61 - 2.72 (m, 3 H) 3.03 (t, J=10.10 Hz, 1 H) 3.35 (s, 3 H) 3.39 (dd, J=10.49, 7.07 Hz, 1 H) 3.53 - 3.63 (m, 2 H) 3.68 (d, J=6.06 Hz, 1 H) 3.76 - 3.84 (m, 1 H) 3.91 - 3.94 (m, 1 H) 3.96 - 4.06 (m, 1 H) 4.55 (d, J=7.15 Hz, 1 H) 4.61 (d, J=14.30 Hz, 1 H) 4.78 (d, J=14.45 Hz, 1 H) 4.85 (d, J=4.04 Hz, 1 H) 4.85 - 4.95 (m, 1 H) 7.25 (s, 1 H) 7.60 (dd, J=8.55, 4.97 Hz, 1 H) 8.25 (dd, J=8.55, 1.71 Hz, 1 H) 9.24 (dd, J=5.05, 1.79 Hz, 1 H)
258					728.4	(300 MHz) : 0.85 (d, J=6.53 Hz, 3 H) 0.86 (d, J=7.15 Hz, 3 H) 0.92 (t, J=7.38 Hz, 3 H) 1.16 - 1.98 (m, 6 H) 1.26 (d, J=6.06 Hz, 3 H) 1.34 (d, J=6.84 Hz, 3 H) 1.43 (d, J=7.31 Hz, 3 H) 1.51 (s, 3 H) 2.08 (dd, J=15.93, 1.32 Hz, 1 H) 2.23 - 2.57 (m, 3 H) 2.29 (s, 6 H) 2.42 (s, 3 H) 3.00 (dd, J=15.47, 2.56 Hz, 1 H) 3.21 (dd, J=10.34, 7.23 Hz, 1 H) 3.33 - 3.57 (m, 3 H) 3.67 (s, 1 H) 3.89 (d, J=9.17 Hz, 1 H) 3.94 - 4.07 (m, 2 H) 4.13 - 4.24 (m, 1 H) 4.41 (d, J=7.31 Hz, 1 H) 4.64 - 4.72 (m, 1 H) 7.22 (s, 1 H) 7.61 (dd, J=8.55, 4.97 Hz, 1 H) 8.25 (dd, J=8.55, 1.71 Hz, 1 H) 9.25 (dd, J=5.05, 1.79 Hz, 1 H)

Example 250

[0804] 

(1) By using the compound obtained in Example 6 (650 mg) as a starting material, a cyclized compound (312 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (300 mg) as a starting material, the compound shown in Table 10 (166 mg) was obtained in the same manner as that of Example 7, (4).

Example 251

[0805] The compound obtained in Example 250 (50 mg) was dissolved in acetonitrile (1.5 ml), the solution was added with 3-bromo-1,5- naphthyridine (21.1 mg) obtained by the method described in the literature (Journal of Organic Chemistry, 1968, vol. 33, p.1384), tetrakistriphenylphosphine palladium (3.9 mg) and triethylamine (0.3 ml), and the mixture was stirred at 80°C for 4 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 10:10:0.2) to obtain the compound shown in Table 10 (26.8 mg).

Example 252

[0806] By using the compound obtained in Example 250 (6.0 mg) and 5-iodo-3-(pyridazin-3-yl)isoxazole (3.3 mg) obtained by the method described in the patent document (WO05/087787) as starting materials, the compound shown in Table 10 (4.24 mg) was obtained in the same manner as that of Example 251.

Example 253

[0807] By using the compound obtained in Example 250 (92 mg) as a starting material, the compound shown in Table 10 (48.3 mg) was obtained in the same manners as those of Example 176, (3), Example 207, (1) and Example 125, (3).

Example 254

[0808] By using the compound obtained in Example 253 (22 mg) as a starting material, the compound shown in Table 10 (10.1 mg) was obtained in the same manner as that of Example 251.

Example 255

[0809] By using the compound obtained in Example 253 (22 mg) as a starting material, the compound shown in Table 10 (21.4 mg) was obtained in the same manner as that of Example 252.

Example 256

[0810] 

(1) By using the compound obtained in Example 255 (15 mg) as a starting material, a 3-hydroxy compound (11.2 mg) was obtained in the same manners as those of Example 125, (2) and Example 176, (3).

(2) By using the compound obtained in (1) mentioned above (11.2 mg) as a starting material, the compound shown in Table 10 (6.71 mg) was obtained in the same manners as those of Example 176, (4) and Example 125, (3).

Example 257

[0811] 

(1) By using the compound obtained in Example 250, (1) (1.0 g) as a starting material, a 9-hydroxy compound (592 mg) was obtained in the same manners as those of Example 126, (1), Example 219, (2) and Example 7, (4).

(2) By using the compound obtained in (1) mentioned above (590 mg) as a starting material, a ketone compound (594 mg) was obtained in the same manners as those of Example 176, (3) and (4).

(3) By using the compound obtained in (2) mentioned above (280 mg) as a starting material, a deacetylated compound (229.5 mg) was obtained in the same manner as that of Example 125, (3).

(4) By using the compound obtained in (3) mentioned above (150 mg) as a starting material, a coupling compound (188 mg) was obtained in the same manner as that of Example 252.

(5) By using the compound obtained in (4) mentioned above (180 mg) as a starting material, an oxime compound (81 mg) was obtained in the same manner as that of Example 214.

(6) By using the compound obtained in (5) mentioned above (49.7 mg) as a starting material, the compound shown in Table 10 (40.0 mg) was obtained in the same manner as that of Example 219, (4).

Example 258

[0812] 

(1) By using the compound obtained in Example 250, (1) (1.0 g) as a starting material, a 3-hydroxy compound (135 mg) was obtained in the same manners as those of Example 125, (2) and Example 112, (1).

(2) By using the compound obtained in (1) mentioned above (135 mg) as a starting material, a 3-ketone compound (72.3 mg) was obtained in the same manners as those of Example 176, (4) and Example 114, (4).

(3) By using the compound obtained in (2) mentioned above (71 mg) as a starting material, a coupling compound (70.6 mg) was obtained in the same manner as that of Example 252.

(4) By using the compound obtained in (3) mentioned above (70.6 mg) as a starting material, the compound shown in Table 10 (38.4 mg) was obtained in the same manner as that of Example 125, (2).

Example 259: Synthesis of the compound represented by the formula (T)

[0813] 

[0814] 

(1) The compound obtained in Example 240, (2) (0.2 g) was dissolved in chloroform (3 ml), the solution was added with trichloroacetyl isocyanate (26 µl) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with methanol (40 µl) and potassium carbonate (40 mg), and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain a 6-O-carbamate compound (0.16 g).

[0815] 

(2) By using the compound obtained in (1) mentioned above (80 mg) as a starting material, the title compound (4.7 mg) was obtained in the same manner as that of Example 7, (4).
MS (ESI) m/z = 778.5 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.85 (d, J=6.22Hz, 3H), 0.90 (d, J=6.68Hz, 3H), 1.13 (d, J=7.15Hz, 3H), 1.15-1.32 (m, 14H), 1.27 (d, J=6.37Hz, 3H), 1.44-1.80 (m, 3H), 2.10-2.61 (m, 6H), 2.29 (s, 6H), 2.32 (s, 3H), 2.76-2.96 (m, 2H), 2.98-3.07 (m, 1H), 3.20-3.33 (m, 2H), 3.33 (s, 3H), 3.42-3.55 (m, 1H), 3.76 (s, 3H), 3.80-4.09 (m, 3H), 4.24-4.49 (m, 3H), 4.73-4.81 (m, 1H)

Example 260: Synthesis of the compound represented by the formula (U)

[0816] 

[0817] 

(1) By using the compound obtained in Example 245, (2) (119 mg) as a starting material, a deprotected compound (70 mg) was obtained in the same manner as that of Example 7, (4).

[0818] 

(2) The compound obtained in (1) mentioned above (30 mg) was dissolved in dichloromethane (860 µl), the solution was added with m-chloroperbenzoic acid (30 mg) on an ice bath, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1). The resulting compound (27 mg) was dissolved in tetrahydrofuran (4 ml), the solution was added with triphenylphosphine (45 mg), and the mixture was stirred at 70°C for 60 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a nitrone compound (24 mg).

[0819] 

(3) The compound obtained in (2) mentioned above (8 mg) was dissolved in diethyl ether-dichloromethane-tetrahydrofuran (1:1:1, 3 ml), the solution was added with a 0.84 M solution of methylmagnesium iodide in ether (660 µl) on an ice bath, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the title compound (5 mg).
MS (ESI) m/z = 735.5 [M+H]^+
1H-NMR (300MHz, CDCl₃) δ (ppm): 0.87 (t, J=7.57Hz, 3H), 0.97 (d, J=6.88Hz, 3H), 1.09-1.13 (m, 6H), 1.18 (d, J=6.88Hz, 3H), 1.19-1.29 (m, 11H), 1.30 (d, J=5.96Hz, 3H), 1.34 (s, 3H), 1.44-1.77 (m, 4H), 1.98-2.05 (m, 1H), 2.06-2.13 (m, 1H), 2.14-2.22 (m, 2H), 2.28 (s, 6H), 2.36 (d, J=15.13Hz, 1H), 2.42-2.52 (m, 1H), 2.73-2.81 (m, 1H), 2.92-3.08 (m, 3H), 3.16-3.25 (m, 2H), 3.30 (s, 3H), 3.30 (s, 3H), 3.42-3.54 (m, 1H), 3.73 (d, J=8.71Hz, 1H), 3.97-4.08 (m, 2H), 4.38 (d, J=7.34Hz, 1H), 4.86 (d, J=4.58Hz, 1H), 4.96 (td, J=7.91, 3.44Hz, 1H), 5.83 (br.s., 1H)

Example 261: Synthesis of the compound represented by the formula (V)

[0820] 

[0821] By using the compound obtained in Example 1 (700 mg) and cis-2,3-epoxybutane (254 mg) as starting materials, the title compound (4.0 mg) was obtained in the same manner as that of Example 7.
MS (ESI) m/z = 719.2 [M+H]⁺

Syntheses of Examples 262 to 551

[0822] Preparation methods of compounds represented by the formula (W) having R^1W and R^2W defined in Table 11 are shown below.

[0823] 

[Table 11-1]

Example	R1W	R2W	ESIMS (M+H)	1H-NMR, CDCl3, δ (ppm)
262			718	(300 MHz): 0.81 - 0.84 (m, 6 H) 0.89 (t, J=7.2 Hz, 3 H) 1.10 (d, J=7.2 Hz, 3 H) 1.15 - 1.23 (m, 10 H) 1.27 - 1.32 (m, 6 H) 1.48 - 1.85 (m, 6 H) 2.15 - 2.54 (m, 16 H) 2.76 - 2.91 (m, 2 H) 3.18 - 3.24 (m, 4 H) 3.29 (s, 3 H) 3.41 - 3.54 (m, 2 H) 3.72 (d, J=7.8 Hz, 1 H) 4.04 (dq, J=9.6 Hz, J=6.3 Hz, 1 H) 4.14 (d, J=4.5 Hz, 1 H) 4.42 (d, J=7.2 Hz, 1 H) 4.65 (m, 1 H) 4.95 (d, J=4.8 Hz, 1 H)
263			719	(300 MHz): 0.81 - 0.92 (m, 9 H) 1.11 (d, J=7.2 Hz, 3 H) 1.16 - 1.25 (m, 13 H) 1.32 (s, 3 H) 1.42 - 1.85 (m, 7 H) 2.07 (d, J=15.3 Hz, 1 H) 2.15 - 2.55 (m, 14 H) 2.77 - 2.91 (m, 2 H) 3.04 (brs, 1 H) 3.17 - 3.24 (m, 4 H) 3.32 (s, 3 H) 3.40 - 3.49 (m, 2 H) 3.67 (d, J=7.5 Hz, 1 H) 4.18 (d, J=3.9 Hz, 1 H) 4.43 (d, J=7.2 Hz, 1 H) 4.58 - 4.64 (m, 2 H) 4.99 (d, J=4.8 Hz, 1 H)
264			967.6	(600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.26 (m, 2 H) 1.10 - 1.20 (m, 15 H) 1.31 (s, 3 H) 1.32 (d, J=6.88 Hz, 3 H) 1.50 - 1.65 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1:80 - 1.88 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.23 - 2.51 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.64 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.16 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.45 (m, 1 H) 3.54 - 3.64 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.79 (s, 3 H) 3.81 - 3.85 (m, 1 H) 4.18 - 4.25 (m, 1 H) 4.35 - 4.42 (m, 1 H) 4.43 - 4.48 (m, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=3.21 Hz, 1 H) 5.19 (s, 1 H) 6.76 (d, J=10.09 Hz, 1 H) 6.84 (s, 1 H) 6.88 (d, J=7.34 Hz, 1 H) 7.21 (t, J=7.79 Hz, 1 H)
265			967.6	(600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.99 (t, J=6.88 Hz, 3 H) 1.07 - 1.23 (m, 2 H) 1.12 (s, 3 H) 1.12 - 1.18 (m, 9 H) 1.19 (d, J=6.42 Hz, 3 H) 1.28 - 1.32 (m, 6 H) 1.50 - 1.66 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.22 - 2.46 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.61 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.91 (m, 1 H) 3.15 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.35 - 3.45 (m, 1 H) 3.56 - 3.65 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.78 (s, 3 H) 3.80 - 3.87 (m, 1 H) 4.21 (s, 1 H) 4.36 - 4.42 (m, 1 H) 4.46 (d, J=7.79 Hz, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.17 - 5.23 (m, 1 H) 6.83 (d, J=8.71 Hz, 2 H) 7.19 (d, J=8.25 Hz, 2 H)

[0824] 

[Table 11-2]

266			955.6	(600 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.25 (m, 2 H) 1.10 (s, 3 H) 1.11 - 1.14 (m, 3 H) 1.14 - 1.20 (m, 9 H) 1.27 - 1.35 (m, 6 H) 1.51 - 1.65 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.81 - 1.88 (m, 1 H) 2.10 - 2.21 (m, 1 H) 2.23 - 2.33 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.47 (m, 4 H) 2.49 - 2.62 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.92 (m, 1 H) 3.15 - 3.26 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.56 - 3.65 (m, 1 H) 3.72 (d, J=7.79 Hz, 1 H) 3.83 - 3.89 (m, 1 H) 4.22 (s, 1 H) 4.35 - 4.43 (m, 1 H) 4.44 - 4.49 (m, 1 H) 4.52 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.15 (s, 1 H) 6.98 (t, J=8.71 Hz, 2 H) 7.23 - 7.29 (m, 2 H)
267			971.6	(600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.25 (m, 2 H) 1.10 - 1.14 (m, 3 H) 1.11 (s, 3 H) 1.14 - 1.20 (m, 9 H) 1.28 - 1.33 (m, 6 H) 1.50 - 1.66 (m, 3 H) 1.69 - 1.80 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.10 - 2.21 (m, 1 H) 2.22 - 2.34 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.37 - 2.48 (m, 4 H) 2.50 - 2.62 (m, 3 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.15 - 3.26 (m, 3 H) 3.23 (s, 3 H) 3.33 - 3.45 (m, 1 H) 3.36 (s, 3 H) 3.55 - 3.65 (m, 1 H) 3.72 (d, J=7.79 Hz, 1 H) 3.82 - 3.89 (m, 1 H) 4.18 - 4.26 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.44 - 4.49 (m, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.15 (s, 1 H) 7.21 - 7.29 (m, 4 H)
268			951.6	(600 MHz): 0.82 (d, J=5.96 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.96 - 1.03 (m, 3 H) 1.07 - 1.25 (m, 17 H) 1.28 - 1.34 (m, 6 H) 1.48 - 1.66 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.30 (m, 2 H) 2.27 (s, 6 H) 2.31 (s, 3 H) 2.33 - 2.48 (m, 4 H) 2.36 (s, 3 H) 2.52 - 2.63 (m, 3 H) 2.78 - 2.85 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.15 - 3.23 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.56 - 3.66 (m, 1 H) 3.72 (d, J=8.25 Hz, 1 H) 3.80 - 3.89 (m, 1 H) 4.16 - 4.25 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.45 - 4.49 (m, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.93 - 5.00 (m, 1 H) 5.22 (s, 1 H) 7.10 (d, J=7.79 Hz, 2 H) 7.17 (d, J=8.25 Hz, 2 H)

[0825] 

[Table 11-3]

269			955.6	(600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=8.02 Hz, 3 H) 1.00 (t, J=6.88 Hz, 3 H) 1.07 - 1.27 (m, 2 H) 1.10 (s, 3 H) 1.12 (d, J=6.88 Hz, 3 H) 1.14 - 1.18 (m, 6 H) 1.19 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.33 (d, J=6.88 Hz, 3 H) 1.49 - 1.68 (m, 3 H) 1.74 (s, 1 H) 1.85 (s, 1 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.50 (m, 6 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.65 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.89 (d, J=16.05 Hz, 1 H) 3.15 - 3.28 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.58 - 3.67 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.17 (s, 1 H) 4.26 - 4.33 (m, 1 H) 4.34 - 4.42 (m, 1 H) 4.49 (d, J=6.42 Hz, 1 H) 4.48 - 4.56 (m, 1 H) 4.64 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.25 - 5.33 (m, 1 H) 6.98 - 7.03 (m, 1 H) 7.08 (t, J=7.11 Hz, 1 H) 7.17 - 7.24 (m, 1 H) 7.30 (t, J=7.11 Hz, 1 H)
270			1043.6	mixture of diastereomers (600 MHz):0.78 (d, J=6.42 Hz, 6 H) 0.86 (t, J=7.34 Hz, 3 H) 0.90 - 1.00 (m, 3 H) 1.04 - 1.22 (m, 2 H) 1.07 - 1.17 (m, 15 H) 1.24 - 1.31 (m, 6 H) 1.46 - 1.63 (m, 3 H) 1.71 (s, 1 H) 1.81 (s, 1 H) 2.07 - 2.17 (m, 1 H) 2.18 - 2.47 (m, 6 H) 2.23 (s, 6 H) 2.32 (s, 3 H) 2.48 - 2.61 (m, 3 H) 2.74 - 2.81 (m, 1 H) 2.85 (d, J=14.21 Hz, 1 H) 3.11 - 3.23 (m, 3 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.33 - 3.43 (m, 1 H) 3.52 - 3.62 (m, 1 H) 3.68 (d, J=7.79 Hz, 1 H) 3.72 - 3.84 (m, 1 H) 4.14 - 4.22 (m, 1 H) 4.32 - 4.40 (m, 1 H) 4.43 (d, J=5.96 Hz, 1 H) 4.47 - 4.54 (m, 1 H) 4.60 (s, 1 H) 4.91 - 4.96 (m, 1 H) 5.00 (s, 2 H) 5.15 - 5.25 (m, 1 H) 6.87 (d, J=8.71 Hz, 2 H) 7.17 (d, J=7.79 Hz, 2 H) 7.26 - 7.31 (m, 1 H) 7.32 - 7.37 (m, 2 H) 7.37 - 7.41 (m, 2 H)
271			955.6	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.79 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.67 (m, 3 H) 1.69 - 1.89 (m, 2 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.63 (m, 9 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.85 (m, 1 H) 2.88 (d, J=15.13 Hz, 1 H) 3.16 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.55 - 3.63 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.78 - 3.88 (m, 1 H) 4.18 - 4.25 (m, 1 H) 4.34 - 4.43 (m, 1 H) 4.43 - 4.48 (m, 1 H) 4.53 (d, J=4.58 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=3.21 Hz, 1 H) 5.14 - 5.21 (m, 1 H) 6.90 (t, J=8.25 Hz, 1 H) 7.01 (d, J=10.09 Hz, 1 H) 7.06 (d, J=7.79 Hz, 1 H) 7.22 - 7.28 (m, 1 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.79 Hz, 3 H) 0.97 (t, J=7.11 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.67 (m, 3 H) 1.69 - 1.89 (m, 2 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.63 (m, 9 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.85 (m, 1 H) 2.88 (d, J=15.13 Hz, 1 H) 3.16 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.55 - 3.63 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.78 - 3.88 (m, 1 H) 4.18 - 4.25 (m, 1 H) 4.34 - 4.43 (m, 1 H) 4.43 - 4.48 (m, 1 H) 4.54 (d, J=4.13 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=3.21 Hz, 1 H) 5.14 - 5.21 (m, 1 H) 6.90 (t, J=8.25 Hz, 1 H) 7.01 (d, J=10.09 Hz, 1 H) 7.06 (d, J=7.79 Hz, 1 H) 7.22 - 7.28 (m, 1 H)

[0826] 

[Table 11-4]

272			971.6	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.87 - 0.93 (m, 3 H) 0.94 - 1.03 (m, 3 H) 1.07 - 1.25 (m, 2 H) 1.11 - 1.21 (m, 15 H) 1.30 (s, 3 H) 1.32 (d, J=6.88 Hz, 3 H) 1.48 - 1.65 (m, 3 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.10 - 2.21 (m, 1 H) 2.21 - 2.53 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.64 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.96 (m, 1 H) 3.16 - 3.26 (m, 3 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.46 (m, 1 H) 3.55 - 3.66 (m, 1 H) 3.69 - 3.74 (m, 1 H) 3.76 - 3.88 (m, 1 H) 4.18 - 4.26 (m, 1 H) 4.34 - 4.42 (m, 1 H) 4.43 - 4.51 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.63 (s, 1 H) 4.93 - 5.00 (m, 1 H) 5.12 - 5.23 (m, 1 H) 7.15 - 7.31 (m, 4 H)
273			981.6	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.79 Hz, 3 H) 0.93 - 1.04 (m, 3 H) 1.06 - 1.27 (m, 2 H) 1.10 - 1.21 (m, 15 H) 1.27 - 1.33 (m, 6 H) 1.39 (t, J=7.34 Hz, 3 H) 1.49 - 1.67 (m, 3 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.16 (s, 1 H) 2.21 - 2.33 (m, 2 H) 2.28 (s, 6 H) 2.33 - 2.49 (m, 4 H) 2.35 (s, 3 H) 2.50 - 2.64 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.92 (m, 1 H) 3.14 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.56 - 3.66 (m, 1 H) 3.69 - 3.74 (m, 1 H) 3.74 - 3.87 (m, 1 H) 3.97 - 4.02 (m, 2 H) 4.18 - 4.24 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.47 (d, J=6.88 Hz, 1 H) 4.51 - 4.55 (m, 1 H) 4.64 (s, 1 H) 4.95 - 4.99 (m, 1 H) 5.18 - 5.28 (m, 1 H) 6.81 (d, J=8.25 Hz, 2 H) 7.18 (d, J=8.25 Hz, 2 H), and (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.79 Hz, 3 H) 0.93 - 1.04 (m, 3 H) 1.06 - 1.27 (m, 2 H) 1.10 - 1.21 (m, 15 H) 1.27 - 1.33 (m, 6 H) 1.39 (t, J=7.34 Hz, 3 H) 1.49 - 1.67 (m, 3 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.16 (s, 1 H) 2.21 - 2.33 (m, 2 H) 2.28 (s, 6 H) 2.33 - 2.49 (m, 4 H) 2.35 (s, 3 H) 2.50 - 2.64 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.92 (m, 1 H) 3.14 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.56 - 3.66 (m, 1 H) 3.69 - 3.74 (m, 1 H) 3.74 - 3.87 (m, 1 H) 3.97 - 4.02 (m, 2 H) 4.18 - 4.24 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.47 (d, J=6.88 Hz, 1 H) 4.51 - 4.55 (m, 1 H) 4.64 (s, 1 H) 4.95 - 4.99 (m, 1 H) 5.18 - 5.28 (m, 1 H) 6.81 (d, J=8.25 Hz, 2 H) 7.18 (d, J=8.25 Hz, 2 H)
274			912.5	mixture of diastereomers (600 MHz):0.78 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 - 1.24 (m, 17 H) 1.29 - 1.34 (m, 6 H) 1.49 - 1.87 (m, 5 H) 2.10 - 2.45 (m, 5 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.54 - 2.60 (m, 1 H) 2.63 - 2.74 (m, 2 H) 2.77 - 2.83 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.17 - 3.44 (m, 10 H) 3.55 - 3.62 (m, 4 H) 3.65 - 3.72 (m, 2 H) 4.16 - 4.22 (m, 1 H) 4.34 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.28 - 5.33 (m, 1 H) 6.01 (br. s., 1 H) 6.46 (br. s., 1 H) 6.51 (br. s., 1 H)
275			951.6	mixture of diastereomers (600 MHz):0.81 (d, J=5.96 Hz, 6 H) 0.86 - 0.93 (m, 3 H) 0.93 - 1.03 (m, 3 H) 1.04 - 1.25 (m, 2 H) 1.09 - 1.20 (m, 15 H) 1.28 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.49 - 1.64 (m, 3 H) 1.74 (s, 1 H) 1.85 (s, 1 H) 2.10 - 2.21 (m, 1 H) 2.23 - 2.46 (m, 4 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.36 (s, 3 H) 2.47 - 2.54 (m, 1 H) 2.54 - 2.69 (m, 4 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.05 - 3.16 (m, 2 H) 3.17 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.55 - 3.66 (m, 1 H) 3.69 - 3.74 (m, 1 H) 3.97 - 4.03 (m, 1 H) 4.16 - 4.25 (m, 1 H) 4.33 - 4.41 (m, 1 H) 4.42 - 4.54 (m, 2 H) 4.64 (s, 1 H) 4.92 - 4.99 (m, 1 H) 5.02 - 5.11 (m, 1 H) 7.07 - 7.19 (m, 3 H) 7.30 - 7.39 (m, 1 H), and (600 MHz): 0.81 (d, J=5.96 Hz, 6 H) 0.86 - 0.93 (m, 3 H) 0.93 - 1.03 (m, 3 H) 1.04 - 1.25 (m, 2 H) 1.09 - 1.20 (m, 15 H) 1.28 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.49 - 1.64 (m, 3 H) 1.74 (s, 1 H) 1.85 (s, 1 H) 2.10 - 2.21 (m, 1 H) 2.23 - 2.46 (m, 4 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.37 (s, 3 H) 2.47 - 2.54 (m, 1 H) 2.54 - 2.69 (m, 4 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.05 - 3.16 (m, 2 H) 3.17 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.55 - 3.66 (m, 1 H) 3.69 - 3.74 (m, 1 H) 4.02 - 4.09 (m, 1 H) 4.16 - 4.25 (m, 1 H) 4.33 - 4.41 (m, 1 H) 4.42 - 4.54 (m, 2 H) 4.64 (s, 1 H) 4.92 - 4.99 (m, 1 H) 5.00 - 5.06 (m, 1 H) 7.07 - 7.19 (m, 3 H) 7.30 - 7.39 (m, 1 H)

[0827] 

[Table 11-5]

276			951.6	mixture of diastereomers (600 MHz): 0.77 (d, J=6.42 Hz, 6 H) 0.84 (t, J=7.57 Hz, 3 H) 0.89 - 0.99 (m, 3 H) 1.01 - 1.22 (m, 2 H) 1.05 - 1.16 (m, 15 H) 1.26 (s, 3 H) 1.27 (d, J=3.67 Hz, 3 H) 1.45 - 1.61 (m, 3 H) 1.70 (s, 1 H) 1.79 (s, 1 H) 2.05 - 2.17 (m, 1 H) 2.16 - 2.47 (m, 6 H) 2.23 (s, 6 H) 2.29 (s, 3 H) 2.31 (s, 3 H) 2.48 - 2.62 (m, 3 H) 2.72 - 2.79 (m, 1 H) 2.84 (d, J=14.67 Hz, 1 H) 3.10 - 3.20 (m, 3 H) 3.18 (s, 3 H) 3.29 (s, 3 H) 3.31 - 3.41 (m, 1 H) 3.50 - 3.61 (m, 1 H) 3.64 - 3.69 (m, 1 H) 3.69 - 3.82 (m, 1 H) 4.13 - 4.20 (m, 1 H) 4.30 - 4.38 (m, 1 H) 4.38 - 4.45 (m, 1 H) 4.45 - 4.51 (m, 1 H) 4.59 (s, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 5.11 - 5.24 (m, 1 H) 6.98 (d, J=7.34 Hz, 1 H) 7.01 - 7.07 (m, 2 H) 7.13 (t, J=7.57 Hz, 1 H)
277			965.6	mixture of diastereomers (600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.57 Hz, 3 H) 0.94 - 1.04 (m, 3 H) 1.06 - 1.28 (m, 2 H) 1.11 - 1.24 (m, 18 H) 1.31 (s, 3 H) 1.31 - 1.35 (m, 3 H) 1.49 - 1.66 (m, 3 H) 1.75 (s, 1 H) 1.85 (s, 1 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.34 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.50 (m, 4 H) 2.53 - 2.63 (m, 3 H) 2.62 (q, J=7.34 Hz, 2 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.16 - 3.23 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.56 - 3.66 (m, 1 H) 3.72 (d, J=8.25 Hz, 1 H) 3.76 - 3.90 (m, 1 H) 4.17 - 4.24 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.44 - 4.50 (m, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.64 (s, 1 H) 4.94 - 5.00 (m, 1 H) 5.25 (s, 1 H) 7.12 (d, J=7.79 Hz, 2 H) 7.19 (d, J=7.79 Hz, 2 H)
278				mixture of diastereomers (600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.94 - 1.06 (m, 3 H) 1.06 - 1.26 (m, 2 H) 1.10 - 1.22 (m, 15 H) 1.30 (s, 3 H) 1.31 - 1.37 (m, 3 H) 1.49 - 1.66 (m, 3 H) 1.70 - 1.80 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.12 - 2.22 (m, 1 H) 2.22 - 2.34 (m, 2 H) 2.28 (s, 6 H) 2.35 - 2.54 (m, 4 H) 2.36 (s, 3 H) 2.53 - 2.69 (m, 3 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.92 (m, 1 H) 2.93 (s, 6 H) 3.15 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.56 - 3.66 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.73 - 3.84 (m, 1 H) 4.17 - 4.26 (m, 1 H) 4.35 - 4.42 (m, 1 H) 4.43 - 4.49 (m, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.59 - 4.69 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.20 - 5.29 (m, 1 H) 6.57 - 6.70 (m, 3 H) 7.16 (t, J=7.79 Hz, 1 H)
279			982.6	mixture of diastereomers (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.87 - 0.92 (m, 3 H) 0.96 - 1.04 (m, 3 H) 1.06 - 1.26 (m, 2 H) 1.10 - 1.20 (m, 15 H) 1.30 (s, 3 H) 1.38 (d, J=6.42 Hz, 3 H) 1.49 - 1.65 (m, 3 H) 1.71 - 1.80 (m, 1 H) 1.79 - 1.88 (m, 1 H) 2.10 - 2.19 (m, 1 H) 2.21 - 2.67 (m, 9 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.94 (m, 1 H) 3.19 - 3.40 (m, 4 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.55 - 3.61 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.91 - 4.01 (m, 1 H) 4.18 - 4.25 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.41 - 4.49 (m, 1 H) 4.51 - 4.56 (m, 1 H) 4.62 (s, 1 H) 4.94 - 4.98 (m, 1 H) 5.08 - 5.16 (m, 1 H) 7.47 (t, J=8.02 Hz, 1 H) 7.68 (d, J=7.79 Hz, 1 H) 8.09 (d, J=8.71 Hz, 1 H) 8.17 (s, 1 H)

[0828] 

[Table 11-6]

280			833.5	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 (t, J=7.11 Hz, 3 H) 1.11 (d, J=7.34 Hz, 3 H) 1.13 - 1.15 (m, 1 H) 1.15 - 1.18 (m, 9 H) 1.19 (d, J=5.96 Hz, 3 H) 1.23 (d, J=11.92 Hz, 1 H) 1.30 (s, 3 H) 1.50 - 1.58 (m, 1 H) 1.60 (dd, J=15.13, 5.04 Hz, 1 H) 1.65 (d, J=13.30 Hz, 1 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.11 - 2.21 (m, 1 H) 2.22 - 2.29 (m, 1 H) 2.30 (s, 6 H) 2.30 - 2.34 (m, 1 H) 2.36 (s, 3 H) 2.36 - 2.47 (m, 1 H) 2.40 (d, J=15.13 Hz, 1 H) 2.55 - 2.67 (m, 3 H) 2.70 - 2.78 (m, 2 H) 2.78 - 2.84 (m, 1 H) 2.89 (d, J=13.30 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.26 - 3.31 (m, 2 H) 3.33 (s, 3 H) 3.40 (s, 1 H) 3.55 - 3.62 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.20 (s, 1 H) 4.33 - 4.41 (m, 1 H) 4.44 (d, J=6.88 Hz, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.28 - 5.36 (m, 1 H)
281			1005.6	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.94 (t, J=7.11 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.29 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.65 (m, 3 H) 1.71 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.10 - 2.19 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.46 - 2.75 (m, 5 H) 2.77 - 2.85 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.15 - 3.26 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.40 (m, 1 H) 3.52 - 3.62 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.07 - 4.15 (m, 1 H) 4.21 - 4.29 (m, 1 H) 4.35 - 4.47 (m, 2 H) 4.54 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.93 - 5.00 (m, 1 H) 5.02 - 5.10 (m, 1 H) 7.30 (t, J=7.57 Hz, 1 H) 7.48 (t, J=7.79 Hz, 1 H) 7.58 (d, J=7.34 Hz, 1 H) 7.77 (d, J=7.79 Hz, 1 H)
282			1005.6	(600 MHz): 0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 0.97 (t, J=7.11 Hz, 3 H) 1.04 - 1.23 (m, 17 H) 1.28 (s, 3 H) 1.33 (d, J=6.88 Hz, 3 H) 1.47 - 1.64 (m, 3 H) 1.68 - 1.77 (m, 1 H) 1.78 - 1.86 (m, 1 H) 2.08 - 2.17 (m, 1 H) 2.20 - 2.50 (m, 6 H) 2.25 (s, 6 H) 2.34 (s, 3 H) 2.50 - 2.61 (m, 3 H) 2.75 - 2.82 (m, 1 H) 2.82 - 2.91 (m, 1 H) 3.13 - 3.24 (m, 3 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.33 - 3.38 (m, 1 H) 3.50 - 3.59 (m, 1 H) 3.69 (d, J=8.71 Hz, 1 H) 3.85 - 3.92 (m, 1 H) 4.15 - 4.26 (m, 1 H) 4.33 - 4.45 (m, 2 H) 4.52 (d, J=10.09 Hz, 1 H) 4.55 - 4.66 (m, 1 H) 4.92 - 4.97 (m, 1 H) 5.08 - 5.15 (m, 1 H) 7.36 - 7.42 (m, 1 H) 7.44 - 7.54 (m, 3 H)
283			1005.6	(600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.34 (d, J=6.42 Hz, 3 H) 1.50 - 1.64 (m, 3 H) 1.70 - 1.79 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.21 - 2.50 (m, 6 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.52 - 2.63 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.16 - 3.30 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.54 - 3.63 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.88 - 3.94 (m, 1 H) 4.23 (s, 1 H) 4.35 - 4.43 (m, 1 H) 4.42 - 4.48 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.97 (d, J=3.67 Hz, 1 H) 5.12 - 5.20 (m, 1 H) 7.43 (d, J=7.79 Hz, 2 H) 7.55 (d, J=8.25 Hz, 2 H)
284			1015.5	(600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.27 - 1.33 (m, 6 H) 1.48 - 1.67 (m, 3 H) 1.69 - 1.80 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.49 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.62 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.16 - 3.27 (m, 3 H) 3.23 (s, 3 H) 3.36 (s, 3 H) 3.38 - 3.47 (m, 1 H) 3.55 - 3.64 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.80 - 3.87 (m, 1 H) 4.22 (s, 1 H) 4.35 - 4.42 (m, 1 H) 4.43 - 4.50 (m, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.63 (s, 1 H) 4.93 - 5.00 (m, 1 H) 5.13 - 5.20 (m, 1 H) 7.18 (d, J=8.25 Hz, 2 H) 7.41 (d, J=8.25 Hz, 2 H)

[0829] 

[Table 11-7]

285			952.6	mixture of diastereomers (600 MHz):0.81 (d, J=5.96 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 0.95 - 1.05 (m, 3 H) 1.06 - 1.26 (m, 17 H) 1.27 - 1.30 (m, 3 H) 1.31 (s, 3 H) 1.49 - 1.68 (m, 3 H) 1.72 - 1.79 (m, 1 H) 1.80 - 1.87 (m, 1 H) 2.12 - 2.18 (m, 1 H) 2.18 - 2.69 (m, 9 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.75 - 2.85 (m, 1 H) 2.86 - 2.94 (m, 1 H) 3.08 - 3.46 (m, 4 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.53 - 3.65 (m, 1 H) 3.66 - 3.80 (m, 2 H) 4.15 - 4.28 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.42 - 4.51 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.57 - 4.69 (m, 1 H) 4.92 - 5.00 (m, 1 H) 5.05 - 5.20 (m, 1 H) 6.51 - 6.56 (m, 1 H) 6.60 - 6.67 (m, 1 H) 6.68 - 6.75 (m, 1 H) 7.06 (t, J=7.57 Hz, 1 H)
286			940.6	mixture of diastereomers (600 MHz):0.78 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.96 - 1.04 (m, 3 H) 1.08 - 1.33 (m, 23 H) 1.49 - 1.78 (m, 4 H) 1.81 - 1.88 (m, 1 H) 2.11 - 2.64 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=15.13 Hz, 1 H) 3.15 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.57 - 3.65 (m, 4 H) 3.71 (d, J=8.25 Hz, 1 H) 3.81 - 3.89 (m, 1 H) 4.17 - 4.23 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.44 - 4.49 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.36 (br. s., 1 H) 5.99 (d, J=7.79 Hz, 1 H) 6.42 (br. s., 1 H) 6.50 (br. s., 1 H), and (600 MHz):0.78 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.96 - 1.04 (m, 3 H) 1.08 - 1.33 (m, 23 H) 1.49 - 1.78 (m, 4 H) 1.81 - 1.88 (m, 1 H) 2.11 - 2.64 (m, 10 H) 2.27 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=15.13 Hz, 1 H) 3.15 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.57 - 3.65 (m, 4 H) 3.71 (d, J=8.25 Hz, 1 H) 3.81 - 3.89 (m, 1 H) 4.17 - 4.23 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.44 - 4.49 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.36 (br. s., 1 H) 5.99 (d, J=7.79 Hz, 1 H) 6.42 (br. s., 1 H) 6.50 (br. s., 1 H)
287			937.6	(600 MHz):0.79 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.17 (m, 13 H) 1.18 (d, J=5.96 Hz, 3 H) 1.20 - 1.26 (m, 1 H) 1.30 (s, 3 H) 1.32 (d, J=6.88 Hz, 3 H) 1.49 - 1.56 (m, 1 H) 1.59 (dd, J=15.13, 5.04 Hz, 1 H) 1.62 - 1.88 (m, 3 H) 2.11 - 2.19 (m, 1 H) 2.22 - 2.27 (m, 2 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.39 (d, J=15.59 Hz, 1 H) 2.41 - 2.47 (m, 3 H) 2.52 - 2.65 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.91 (m, 1 H) 3.16 - 3.22 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.42 (m, 1 H) 3.57 - 3.64 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.87 (q, J=6.88 Hz, 1 H) 4.17 - 4.24 (m, 1 H) 4.34 - 4.42 (m, 1 H) 4.46 (d, J=7.34 Hz, 1 H) 4.52 (d, J=9.63 Hz, 1 H) 4.60 - 4.66 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 5.18 - 5.24 (m, 1 H) 7.18 - 7.23 (m, 1 H) 7.27 - 7.30 (m, 4 H)
288			987.7	(600 MHz):0.79 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.06 (s, 3 H) 1.08 - 1.18 (m, 13 H) 1.18 - 1.25 (m, 1 H) 1.29 (s, 3 H) 1.45 (d, J=6.42 Hz, 3 H) 1.49 - 1.62 (m, 3 H) 1.69 - 1.88 (m, 2 H) 2.11 - 2.19 (m, 1 H) 2.20 - 2.32 (m, 2 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.38 - 2.48 (m, 2 H) 2.50 - 2.62 (m, 2 H) 2.64 - 2.73 (m, 3 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=15.13 Hz, 1 H) 3.00 - 3.12 (m, 1 H) 3.17 - 3.22 (m, 1 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.48 - 3.55 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.16 - 4.26 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.42 (d, J=6.88 Hz, 1 H) 4.48 (d, J=10.09 Hz, 1 H) 4.59 - 4.67 (m, 2 H) 4.95 (d, J=4.58 Hz, 1 H) 4.98 - 5.04 (m, 1 H) 7.38 - 7.43 (m, 2 H) 7.43 - 7.47 (m, 1 H) 7.48 - 7.54 (m, 2 H) 7.73 (d, J=8.25 Hz, 1 H) 7.83 (d, J=8.25 Hz, 1 H) 8.34 (d, J=8.71 Hz, 1 H)

[0830] 

[Table 11-8]

289			987.7	(600 MHz):0.79 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.02 (t, J=7.11 Hz, 3 H) 1.06 (s, 3 H) 1.13 (d, J=7.34 Hz, 8 H) 1.13 (d, J=7.34 Hz, 3 H) 1.19 - 1.27 (m, 1 H) 1.30 (s, 3 H) 1.42 (d, J=6.42 Hz, 3 H) 1.49 - 1.64 (m, 2 H) 1.58 (dd, J=15.13, 5.04 Hz, 1 H) 1.68 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.25 (m, 1 H) 2.26 (s, 6 H) 2.28 - 2.32 (m, 1 H) 2.35 (s, 3 H) 2.39 (d, J=15.13 Hz, 1 H) 2.46 - 2.55 (m, 3 H) 2.56 - 2.67 (m, 3 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=14.21 Hz, 1 H) 3.17 - 3.23 (m, 3 H) 3.23 (s, 3 H) 3.36 (s, 3 H) 3.37 - 3.42 (m, 1 H) 3.57 - 3.64 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 4.03 (q, J=6.42 Hz, 1 H) 4.17 - 4.24 (m, 1 H) 4.35 - 4.43 (m, 1 H) 4.47 (d, J=6.88 Hz, 1 H) 4.51 (d, J=10.09 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 5.19 - 5.23 (m, 1 H) 7.40 - 7.51 (m, 3 H) 7.67 (s, 1 H) 7.74 - 7.83 (m, 3 H)
290			912.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 17 H) 1.30 (s, 3 H) 1.36 - 1.39 (m, 3 H) 1.50 - 1.87 (m, 5 H) 2.12 - 2.46 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.61 (m, 1 H) 2.66 - 2.73 (m, 2 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.17 - 3.44 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.53 - 3.59 (m, 1 H) 3.61 (s, 3 H) 3.70 (d, J=8.25 Hz, 1 H) 3.82 - 3.87 (m, 1 H) 4.19 - 4.24 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.17 - 5.20 (m, 1 H) 5.96 - 5.98 (m, 1 H) 6.03 - 6.04 (m, 1 H) 6.51 - 6.53 (m, 1 H)
291			987.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.32 (d, J=6.42 Hz, 3 H) 1.50 - 1.87 (m, 5 H) 2.11 - 2.46 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.50 - 2.66 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.91 (m, 1 H) 3.04 (s, 3 H) 3.17 - 3.44 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.60 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 3.82 - 3.88 (m, 1 H) 4.20 - 4.26 (m, 1 H) 4.35 - 4.45 (m, 2 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.95 - 4.99 (m, 1 H) 5.15 - 5.20 (m, 1 H) 7.47 - 7.51 (m, 2 H) 7.85 - 7.89 (m, 2 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.32 (d, J=6.42 Hz, 3 H) 1.50 - 1.87 (m, 5 H) 2.11 - 2.46 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.50 - 2.66 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.91 (m, 1 H) 3.04 (s, 3 H) 3.17 - 3.44 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.60 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 3.82 - 3.88 (m, 1 H) 4.20 - 4.26 (m, 1 H) 4.35 - 4.45 (m, 2 H) 4.52 - 4.56 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.95 - 4.99 (m, 1 H) 5.15 - 5.20 (m, 1 H) 7.47 - 7.51 (m, 2 H) 7.85 - 7.89 (m, 2 H)
292			927.7	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 17 H) 1.30 (s, 3 H) 1.37 (d, J=6.42 Hz, 3 H) 1.42 (t, J=7.34 Hz, 3 H) 1.49 - 1.87 (m, 5 H) 2.11 - 2.45 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.60 (m, 1 H) 2.63 - 2.70 (m, 2 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.16 - 3.45 (m, 10 H) 3.52 - 3.59 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 3.90 - 3.95 (m, 1 H) 4.16 (q, J=7.18 Hz, 2 H) 4.20 - 4.25 (m, 1 H) 4.34 - 4.45 (m, 2 H) 4.52 - 4.55 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.15 - 5.18 (m, 1 H) 6.07 - 6.08 (m, 1 H) 7.40 - 7.42 (m, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 17 H) 1.30 (s, 3 H) 1.38 (d, J=6.88 Hz, 3 H) 1.42 (t, J=7.11 Hz, 3 H) 1.49 - 1.87 (m, 5 H) 2.11 - 2.45 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.60 (m, 1 H) 2.63 - 2.70 (m, 2 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.16 - 3.45 (m, 10 H) 3.52 - 3.59 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 3.90 - 3.95 (m, 1 H) 4.16 (q, J=7.18 Hz, 2 H) 4.20 - 4.25 (m, 1 H) 4.34 - 4.45 (m, 2 H) 4.52 - 4.55 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.15 - 5.18 (m, 1 H) 6.07 - 6.08 (m, 1 H) 7.40 - 7.42 (m, 1 H)

[0831] 

[Table 11-9]

293			940.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.03 (t, J=7.11 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.26 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.50 - 1.87 (m, 5 H) 2.10 - 2.63 (m, 10 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.78 - 3.11 (m, 4 H) 3.18 - 3.23 (m, 1 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.51 - 3.57 (m, 1 H) 3.66 (s, 3 H) 3.70 (d, J=7.79 Hz, 1 H) 3.96 - 4.04 (m, 1 H) 4.18 - 4.24 (m, 1 H) 4.33 - 4.39 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.47 - 4.51 (m, 1 H) 4.60 - 4.71 (m, 2 H) 4.94 - 4.98 (m, 1 H) 5.98 - 6.02 (m, 2 H) 6.52 - 6.56 (m, 1 H), and (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.99 (t, J=7.11 Hz, 3 H) 1.06 - 1.24 (m, 17 H) 1.26 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.49 - 1.88 (m, 5 H) 2.10 - 2.64 (m, 10 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.77 - 3.11 (m, 4 H) 3.17 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.51 - 3.58 (m, 1 H) 3.65 (s, 3 H) 3.70 (d, J=7.79 Hz, 1 H) 3.96 - 4.04 (m, 1 H) 4.17 - 4.25 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.47 - 4.51 (m, 1 H) 4.60 - 4.66 (m, 1 H) 4.85 - 4.89 (m, 1 H) 4.94 - 4.97 (m, 1 H) 5.99 - 6.02 (m, 2 H) 6.52 - 6.56 (m, 1 H)
294			1008.6	mixture of diastereomers (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 17 H) 1.30 (s, 3 H) 1.37 - 1.41 (m, 3 H) 1.48 - 1.86 (m, 5 H) 2.10 - 2.47 (m, 5 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.55 - 2.73 (m, 3 H) 2.70 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.31 (m, 3 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.52 - 3.61 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 4.17 - 4.24 (m, 1 H) 4.34 - 4.53 (m, 4 H) 4.60 - 4.65 (m, 1 H) 4.95 - 4.98 (m, 1 H) 5.23 - 5.29 (m, 1 H) 7.12 - 7.15 (m, 1 H) 7.44 - 7.46 (m, 1 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 17 H) 1.30 (s, 3 H) 1.37 - 1.41 (m, 3 H) 1.48 - 1.86 (m, 5 H) 2.10 - 2.47 (m, 5 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.55 - 2.73 (m, 3 H) 2.70 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.31 (m, 3 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.52 - 3.61 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 4.17 - 4.24 (m, 1 H) 4.34 - 4.53 (m, 4 H) 4.60 - 4.65 (m, 1 H) 4.95 - 4.98 (m, 1 H) 5.23 - 5.29 (m, 1 H) 7.12 - 7.15 (m, 1 H) 7.44 - 7.46 (m, 1 H)
295			1015.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.95 - 1.01 (m, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.35 (d, J=6.88 Hz, 3 H) 1.49 - 1.87 (m, 5 H) 2.10 - 2.64 (m, 10 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=15.59 Hz, 1 H) 3.04 (s, 3 H) 3.17 - 3.26 (m, 3 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.41 - 3.46 (m, 1 H) 3.54 - 3.60 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.88 - 3.95 (m, 1 H) 4.22 - 4.27 (m, 1 H) 4.36 - 4.46 (m, 2 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.66 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.12 - 5.15 (m, 1 H) 7.52 (d, J=8.71 Hz, 2 H) 7.86 (d, J=8.25 Hz, 2 H)
296			955.8	mixture of diastereomers (600 MHz):0.80 (d, J=6.42 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.03 (t, J=7.11 Hz, 3 H) 1.05-1.25 (m, 17 H) 1.27 - 1.32 (m, 6 H) 1.40 - 1.45 (m, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.59 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.76 - 3.21 (m, 5 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.49 - 3.58 (m, 1 H) 3.69 (d, J=7.34 Hz, 1 H) 4.00 - 4.06 (m, 1 H) 4.13 - 4.45 (m, 5 H) 4.49 - 4.53 (m, 1 H) 4.59 - 4.66 (m, 1 H) 4.88 - 4.92 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 6.09 (s, 1 H) 7.39 (s, 1 H), and (600 MHz):0.80 (d, J=6.42 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 0.99 (t, J=7.11 Hz, 3 H) 1.15 (d, 17 H) 1.27 - 1.32 (m, 6 H) 1.40 - 1.45 (m, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.59 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.76 - 3.21 (m, 5 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.49 - 3.58 (m, 1 H) 3.69 (d, J=7.34 Hz, 1 H) 4.00 - 4.06 (m, 1 H) 4.13 - 4.45 (m, 5 H) 4.49 - 4.53 (m, 1 H) 4.59 - 4.66 (m, 1 H) 4.84 - 4.88 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 6.09 (s, 1 H) 7.39 (s, 1 H)

[0832] 

[Table 11-10]

297			913.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08-1.27 (m, 17 H) 1.30 (s, 3 H) 1.37 (d, J=6.42 Hz, 3 H) 1.47 - 1.87 (m, 5 H) 2.10 - 2.46 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.52 - 2.70 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.17 - 3.46 (m, 3 H) 3.22 (s, 4 H) 3.33 (s, 3 H) 3.53 - 3.60 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.86 (s, 3 H) 3.90 - 3.96 (m, 1 H) 4.19 - 4.26 (m, 1 H) 4.35 - 4.46 (m, 2 H) 4.51 - 4.56 (m, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.15 - 5.19 (m, 1 H) 6.08 - 6.10 (m, 1 H) 7.36 - 7.38 (m, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08- 1.27 (m, 17 H) 1.30 (s, 3 H) 1.37 (d, J=6.42 Hz, 3 H) 1.47 - 1.87 (m, 5 H) 2.10 - 2.46 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.52 - 2.70 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.17 - 3.46 (m, 3 H) 3.22 (s, 4 H) 3.33 (s, 3 H) 3.53 - 3.60 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.86 (s, 3 H) 3.90 - 3.96 (m, 1 H) 4.19 - 4.26 (m, 1 H) 4.35 - 4.46 (m, 2 H) 4.51 - 4.56 (m, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.15 - 5.19 (m, 1 H) 6.08 - 6.10 (m, 1 H) 7.36 - 7.38 (m, 1 H)
298			927.7	mixture of diastereomers (600 MHz):0.76 (d, J=6.42 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.01-1.20 (m, 17 H) 1.25 (s, 3 H) 1.29 (d, J=6.42 Hz, 3 H) 1.44 - 1.81 (m, 5 H) 2.03 - 2.41 (m, 5 H) 2.15 (s, 3 H) 2.24 (s, 6 H) 2.31 (s, 3 H) 2.48 - 2.55 (m, 1 H) 2.59 - 2.63 (m, 2 H) 2.73 - 2.78 (m, 1 H) 2.80 - 2.86 (m, 1 H) 3.12 - 3.39 (m, 4 H) 3.17 (s, 3 H) 3.28 (s, 3 H) 3.47 - 3.54 (m, 1 H) 3.65 (d, J=8.25 Hz, 1 H) 3.72 (s, 3 H) 3.78 - 3.84 (m, 1 H) 4.14 - 4.20 (m, 1 H) 4.29 - 4.41 (m, 2 H) 4.47 - 4.50 (m, 1 H) 4.55 - 4.62 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 5.09 - 5.14 (m, 1 H) 5.81 (s, 1 H), and (600 MHz):0.76 (d, J=6.42 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.01- 1.20 (m, 17 H) 1.25 (s, 3 H) 1.29 (d, J=6.42 Hz, 3 H) 1.44 - 1.81 (m, 5 H) 2.03 - 2.41 (m, 5 H) 2.15 (s, 3 H) 2.24 (s, 6 H) 2.31 (s, 3 H) 2.48 - 2.55 (m, 1 H) 2.59 - 2.63 (m, 2 H) 2.73 - 2.78 (m, 1 H) 2.80 - 2.86 (m, 1 H) 3.12 - 3.39 (m, 4 H) 3.17 (s, 3 H) 3.28 (s, 3 H) 3.47 - 3.54 (m, 1 H) 3.65 (d, J=8.25 Hz, 1 H) 3.72 (s, 3 H) 3.78 - 3.84 (m, 1 H) 4.14 - 4.20 (m, 1 H) 4.29 - 4.41 (m, 2 H) 4.47 - 4.50 (m, 1 H) 4.55 - 4.62 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 5.09 - 5.14 (m, 1 H) 5.81 (s, 1 H)
299			1024.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.02 - 1.07 (m, 6 H) 1.07-1.25 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.49 - 1.88 (m, 5 H) 2.09 - 2.61 (m, 12 H) 2.26 - 2.31 (m, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=13.76 Hz, 1 H) 3.12 - 3.44 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.62 (m, 3 H) 3.66 - 3.72 (m, 2 H) 3.79 (s, 3 H) 4.17 - 4.24 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.25 - 5.33 (m, 1 H) 6.79 (d, J=8.25 Hz, 1 H) 7.09 (d, J=6.42 Hz, 1 H) 7.28 (s, 1 H), and (600 MHz): 0.81 (d, J=8.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.02 - 1.07 (m, 6 H) 1.07-1.25 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.49 - 1.88 (m, 5 H) 2.09 - 2.61 (m, 12 H) 2.26 - 2.31 (m, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.88 (d, J=13.78 Hz, 1 H) 3.12 - 3.44 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.53 - 3.62 (m, 3 H) 3.66 - 3.72 (m, 2 H) 3.79 (s, 3 H) 4.17 - 4.24 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.25 - 5.33 (m, 1 H) 6.79 (d, J=8.25 Hz, 1 H) 7.09 (d, J=6.42 Hz, 1 H) 7.28 (s, 1 H)

[0833] 

[Table 11-11]

300				mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07-1.25 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.87 (m, 9 H) 2.11 - 2.61 (m, 12 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.54 - 3.73 (m, 5 H) 3.80 (s, 3 H) 4.18 - 4.24 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.41 - 4.46 (m, 1 H) 4.50 - 4.56 (m, 1 H) 4.60 - 4.68 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.25 - 5.32 (m, 1 H) 6.80 (d, J=8.25 Hz, 1 H) 7.11 (d, J=9.63 Hz, 1 H) 7.22 (s, 1 H), and (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07-1.25 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.87 (m, 9 H) 2.11 - 2.61 (m, 12 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.54 - 3.73 (m, 5 H) 3.80 (s, 3 H) 4.18 - 4.24 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.41 - 4.46 (m, 1 H) 4.50 - 4.56 (m, 1 H) 4.60 - 4.68 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.25 - 5.32 (m, 1 H) 6.80 (d, J=8.25 Hz, 1 H) 7.11 (d, J=9.63 Hz, 1 H) 7.22 (s, 1 H)
301			1036.7	mixture of diastereomers (600 MHz):0.78 - 0.86 (m, 6 H) 0.86 - 0.95 (m, 6 H) 1.07 - 1.25 (m, 17 H) 1.28 - 1.31 (m, 3 H) 1.33 - 1.37 (m, 3 H) 1.49 - 1.89 (m, 5 H) 2.12 - 2.59 (m, 18 H) 2.61 (s, 3 H) 2.74 - 2.91 (m. 3 H) 3.17 - 3.46 (m, 4 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.54 - 3.73 (m, 2 H) 4.10 - 4.21 (m, 1 H) 4.37 - 4.55 (m, 3 H) 4.61 - 4.78 (m, 2 H) 4.95 - 4.98 (m, 1 H) 5.39 - 5.44 (m, 1 H) 7.14 - 7.18 (m, 1 H) 7.44 - 7.47 (m, 1 H), and (600 MHz):0.78 - 0.86 (m, 6 H) 0.86 - 0.95 (m, 6 H) 1.07 - 1.25 (m, 17 H) 1.28 - 1.31 (m, 3 H) 1.33 - 1.37 (m, 3 H) 1.49 - 1.89 (m, 5 H) 2.12 - 2.59 (m, 18 H) 2.60 (s, 3 H) 2.74 - 2.91 (m, 3 H) 3.17 - 3.46 (m, 4 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.54 - 3.73 (m, 2 H) 4.10 - 4.21 (m, 1 H) 4.37 - 4.55 (m, 3 H) 4.61 - 4.78 (m, 2 H) 4.95 - 4.98 (m, 1 H) 5.73 - 5.80 (m, 1 H) 7.14 - 7.18 (m, 1 H) 7.44 - 7.47 (m, 1 H)
302			941.8	mixture of diastereomers (600 MHz):0.76 (d, J=6.88 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 0.98 (t, J=7.34 Hz, 3 H) 1.01 - 1.21 (m, 17 H) 1.23 - 1.27 (m, 6 H) 1.44 - 1.81 (m, 5 H) 2.05 - 2.56 (m, 10 H) 2.24 (s, 6 H) 2.30 (s, 3 H) 2.71 - 2.79 (m, 1 H) 2.79 - 2.86 (m, 1 H) 2.88 - 3.16 (m, 3 H) 3.16 (s, 3 H) 3.27 (d, J=7.34 Hz, 3 H) 3.31 - 3.39 (m, 1 H) 3.46 - 3.52 (m, 1 H) 3.64 (d, J=9.63 Hz, 1 H) 3.84 (s, 3 H) 3.95 - 4.02 (m, 1 H) 4.13 - 4.19 (m, 1 H) 4.28 - 4.34 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.43 - 4.50 (m, 1 H) 4.53 - 4.60 (m, 1 H) 4.80 - 4.88 (m, 1 H) 4.91 (d, J=5.04 Hz, 1 H) 6.05 (s, 1 H) 7.30 (s, 1 H), and (600 MHz):0.76 (d, J=6.88 Hz, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 0.94 (t, J=7.11 Hz, 3 H) 1.01 - 1.21 (m, 17 H) 1.23 - 1.27 (m, 6 H) 1.44 - 1.81 (m, 5 H) 2.05 - 2.56 (m, 10 H) 2.24 (s, 6 H) 2.30 (s, 3 H) 2.71 - 2.79 (m, 1 H) 2.79 - 2.86 (m, 1 H) 2.88 - 3.16 (m, 3 H) 3.16 (s, 3 H) 3.26 (s, 3 H) 3.31 - 3.39 (m, 1 H) 3.46 - 3.52 (m, 1 H) 3.64 (d, J=9.63 Hz, 1 H) 3.84 (s, 3 H) 3.95 - 4.02 (m, 1 H) 4.13 - 4.19 (m, 1 H) 4.28 - 4.34 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.43 - 4.50 (m, 1 H) 4.53 - 4.60 (m, 1 H) 4.80 - 4.88 (m, 1 H) 4.91 (d, J=5.04 Hz, 1 H) 6.05 (s, 1 H) 7.30 (s, 1 H)

[0834] 

[Table 11-12]

303			955.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.02 (t, J=7.11 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.25 - 1.28 (m, 3 H) 1.30 (s, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.59 (m, 10 H) 2.20 (s, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.83 (m, 1 H) 2.85 - 2.91 (m, 1 H) 2.96 - 3.21 (m, 3 H) 3.21 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.51 - 3.57 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 3.81 (s, 3 H) 3.93 - 3.99 (m, 1 H) 4.19 - 4.25 (m, 1 H) 4.33 - 4.39 (m, 1 H) 4.40 - 4.45 (m, 1 H) 4.49 - 4.53 (m, 1 H) 4.59 - 4.66 (m, 1 H) 4.88 - 4.94 (m, 1 H) 4.96 (d, J=4.58 Hz, 1 H) 5.87 (s, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 0.99 (t, J=7.11 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.25 - 1.28 (m, 3 H) 1.30 (s, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.59 (m, 10 H) 2.20 (s, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.83 (m, 1 H) 2.85 - 2.91 (m, 1 H) 2.96 - 3.21 (m, 3 H) 3.21 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.51 - 3.57 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 3.80 (s, 3 H) 3.93 - 3.99 (m, 1 H) 4.19 - 4.25 (m, 1 H) 4.33 - 4.39 (m, 1 H) 4.40 - 4.45 (m, 1 H) 4.49 - 4.53 (m, 1 H) 4.59 - 4.66 (m, 1 H) 4.88 - 4.94 (m, 1 H) 4.96 (d, J=4.58 Hz, 1 H) 5.87 (s, 1 H)
304			1052.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.96 - 1.00 (m, 3 H) 1.04 (t, J=7.11 Hz, 6 H) 1.07-1.25 (m, 17 H) 1.30 (s, 3 H) 1.31 - 1.34 (m, 3 H) 1.49 - 1.86 (m, 5 H) 2.11 - 2.66 (m, 14 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.91 (m, 2 H) 3.16 - 3.21 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.54 - 3.58 (m, 3 H) 3.71 (d, J=8.25 Hz, 1 H) 3.79 (s, 3 H) 3.80 - 3.84 (m, 1 H) 4.19 - 4.25 (m, 1 H) 4.36 - 4.47 (m, 2 H) 4.53 - 4.56 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.27 - 5.30 (m, 1 H) 6.77 (d, J=7.34 Hz, 1 H) 7.10 (d, J=8.25 Hz, 1 H) 7.29 (s, 1 H), and (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.94 - 0.99 (m, 3 H) 1.04 (t, J=7.11 Hz, 6 H) 1.07-1.25 (m, 17 H) 1.30 (s, 3 H) 1.31 - 1.34 (m, 3 H) 1.49 - 1.86 (m, 5 H) 2.11 - 2.66 (m, 14 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.91 (m, 2 H) 3.16 - 3.21 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.54 - 3.58 (m, 3 H) 3.71 (d, J=8.25 Hz, 1 H) 3.79 (s, 3 H) 3.80 - 3.84 (m, 1 H) 4.19 - 4.25 (m, 1 H) 4.36 - 4.47 (m, 2 H) 4.53 - 4.56 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.27 - 5.30 (m, 1 H) 6.77 (d, J=7.34 Hz, 1 H) 7.10 (d, J=8.25 Hz, 1 H) 7.29 (s, 1 H)
305			1050.8	mixture of diastereomers (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.95 - 1.02 (m, 3 H) 1.04 - 1.35 (m, 23 H) 1.49 - 1.91 (m, 9 H) 2.11 - 2.73 (m, 14 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.92 (m, 2 H) 3.16 - 3.42 (m, 6 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.55 - 3.63 (m, 1 H) 3.69 - 3.73 (m, 1 H) 3.79 - 3.83 (m, 4 H) 4.20 - 4.26 (m, 1 H) 4.36 - 4.49 (m, 2 H) 4.52 - 4.56 (m, 1 H) 4.60-4.68 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.33 - 5.41 (m, 1 H) 6.78 - 6.84 (m, 1 H) 7.14 - 7.22 (m, 1 H) 7.30 - 7.36 (m, 1 H)
306			925.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.39 - 1.44 (m, 3 H) 1.49 - 1.88 (m, 5 H) 2.11 - 2.18 (m, 1 H) 2.22 - 2.46 (m, 4 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.64 (m, 1 H) 2.65 - 2.74 (m, 1 H) 2.75 - 2.85 (m, 2 H) 2.86 - 2.93 (m, 1 H) 3.15 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.50 - 3.61 (m, 1 H) 3.67 - 3.72 (m, 1 H) 3.90 - 3.97 (m, 1 H) 4.18 - 4.27 (m, 1 H) 4.34 - 4.46 (m, 2 H) 4.54 (d, J=10.09 Hz, 1 H) 4.59 - 4.67 (m, 1 H) 4.98 (d, J=4.59 Hz, 1 H) 5.01 - 5.07 (m, 1 H) 6.72 - 6.79 (m, 2 H) 6.90 - 6.96 (m, 1 H) 7.09 - 7.15 (m, 1 H)

[0835] 

[Table 11-13]

307			954.6	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.26 (m, 2 H) 1.10 - 1.20 (m, 15 H) 1.31 (s, 3 H) 1.40 (d, J=6.42 Hz, 3 H) 1.47 - 1.67 (m, 3 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.10 - 2.20 (m, 1 H) 2.22 - 2.45 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.47 - 2.54 (m, 1 H) 2.55 - 2.65 (m, 2 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=14.67 Hz, 1 H) 3.15 - 3.31 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.46 (m, 1 H) 3.57 (s, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.21 - 4.23 (m, 1 H) 4.23 - 4.29 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.50 - 4.56 (m, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.12 - 5.21 (m, 1 H) 7.34 - 7.39 (m, 1 H) 7.53 - 7.60 (m, 1 H) 7.68 (d, J=8.71 Hz, 1 H) 7.74 (d, J=7.79 Hz, 1 H)
308			943.6	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.26 (m, 2 H) 1.10 - 1.20 (m, 15 H) 1.29 - 1.34 (m, 6 H) 1.48 - 1.66 (m, 3 H) 1.75 (s, 1 H) 1.84 (s, 1 H) 2.10 - 2.20 (m, 1 H) 2.20 - 2.47 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.65 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.89 (d, J=14.67 Hz, 1 H) 3.16 - 3.33 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.58 (s, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.21 (s, 1 H) 4.22 - 4.27 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.51 - 4.56 (m, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.21 - 5.30 (m, 1 H) 7.13 - 7.18 (m, 1 H) 7.21 - 7.25 (m, 1 H) 7.29 - 7.34 (m, 1 H) 7.38 - 7.42 (m, 1 H)
309			925.6	mixture of diastereomers (600 MHz):0.77 - 0.85 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.03 - 1.37 (m, 23 H) 1.49 - 1.90 (m, 5 H) 2.09 - 2.53 (m, 5 H) 2.36 (s, 3 H) 2.38 - 2.45 (m, 6 H) 2.55 - 2.62 (m, 1 H) 2.70 - 2.96 (m, 3 H) 3.00 - 3.10 (m, 1 H) 3.21 (s, 3 H) 3.29 - 3.48 (m, 4 H) 3.36 (s, 3 H) 3.58 - 3.74 (m, 3 H) 4.08 - 4.17 (m, 1 H) 4.29 - 4.38 (m, 1 H) 4.46 - 4.55 (m, 2 H) 4.57 - 4.66 (m, 1 H) 4.93 - 4.98 (m, 1 H) 5.28 - 5.35 (m, 1 H) 6.67 - 6.76 (m, 2 H) 6.86 - 6.93 (m, 1 H) 7.09 - 7.17 (m, 1 H), and (600 MHz):0.77 - 0.85 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.03 - 1.37 (m, 23 H) 1.49 - 1.90 (m, 5 H) 2.09 - 2.53 (m, 5 H) 2.36 (s, 3 H) 2.38 - 2.45 (m, 6 H) 2.55 - 2.62 (m, 1 H) 2.70 - 2.96 (m, 3 H) 3.00 - 3.10 (m, 1 H) 3.22 (s, 3 H) 3.29 - 3.48 (m, 4 H) 3.34 (s, 3 H) 3.58 - 3.74 (m, 3 H) 4.08 - 4.17 (m, 1 H) 4.29 - 4.38 (m, 1 H) 4.46 - 4.55 (m, 2 H) 4.57 - 4.66 (m, 1 H) 4.93 - 4.98 (m, 1 H) 5.01 - 5.07 (m, 1 H) 6.67 - 6.76 (m, 2 H) 6.86 - 6.93 (m, 1 H) 7.09 - 7.17 (m, 1 H)
310			953.7	mixture of diastereomers (600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.34 (d, J=5.50 Hz, 3 H) 1.41 (t, J=7.11 Hz, 3 H) 1.47 - 1.71 (m, 3 H) 1.71 - 1.88 (m, 2 H) 2.09 - 2.47 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.64 (m, 3 H) 2.77 - 2.85 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.14 - 3.36 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.53 - 3.64 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.99 - 4.08 (m, 3 H) 4.14 - 4.22 (m, 1 H) 4.32 - 4.41 (m, 1 H) 4.42 - 4.48 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.60 - 4.68 (m, 1 H) 4.97 (d, J=4.13 Hz, 1 H) 5.33 - 5.41 (m, 1 H) 6.83 (d, J=7.79 Hz, 1 H) 6.87 - 6.92 (m, 1 H) 7.14 - 7.22 (m, 2 H)

[0836] 

[Table 11-14]

311			982.7	mixture of diastereomers (600 MHz):0.77 - 0.85 (m, 6 H) 0.86 - 0.92 (m, 6 H) 1.05 - 1.24 (m, 17 H) 1.30 (s, 3 H) 1.34 (d, J=6.42 Hz, 3 H) 1.48 - 1.89 (m, 5 H) 2.08 - 2.66 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.92 (m, 1 H) 2.97 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.35 (s, 3 H) 3.59 - 3.75 (m, 2 H) 4.08 - 4.13 (m, 1 H) 4.32 - 4.57 (m, 4 H) 4.58 - 4.69 (m, 1 H) 4.92 - 4.99 (m, 1 H) 5.22 - 5.27 (m, 1 H) 7.32 - 7.38 (m, 1 H) 7.45 - 7.60 (m, 3 H), and (600 MHz):0.77 - 0.85 (m, 6 H) 0.86 - 0.92 (m, 6 H) 1.05 - 1.24 (m, 17 H) 1.31 (s, 3 H) 1.36 (d, J=6.88 Hz, 3 H) 1.48 - 1.89 (m, 5 H) 2.08 - 2.66 (m, 10 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.77 - 2.84 (m, 1 H) 2.84 - 2.92 (m, 1 H) 2.97 - 3.48 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.59 - 3.75 (m, 2 H) 4.13 - 4.19 (m, 1 H) 4.32 - 4.57 (m, 4 H) 4.58 - 4.69 (m, 1 H) 4.92 - 4.99 (m, 1 H) 5.14 - 5.20 (m, 1 H) 7.32 - 7.38 (m, 1 H) 7.45 - 7.60 (m, 3 H)
312			954.7	mixture of diastereomers (600 MHz):0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.04 - 1.23 (m, 17 H) 1.28 (s, 3 H) 1.29 - 1.32 (m, 3 H) 1.44 - 1.67 (m, 3 H) 1.67 - 1.85 (m, 2 H) 2.06 - 2.45 (m, 6 H) 2.26 (s, 6 H) 2.33 (s, 3 H) 2.46 - 2.54 (m, 1 H) 2.57 - 2.66 (m, 1 H) 2.74 - 2.91 (m, 2 H) 3.13 - 3.42 (m, 4 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.49 - 3.58 (m, 1 H) 3.67 (d, J=7.79 Hz, 1 H) 3.82 - 3.88 (m, 1 H) 4.15 - 4.25 (m, 1 H) 4.30 - 4.45 (m, 2 H) 4.48 - 4.53 (m, 1 H) 4.56 - 4.64 (m, 1 H) 4.95 (d, J=4.58 Hz, 1 H) 5.12 - 5.19 (m, 1 H) 7.44 (d, J=8.71 Hz, 2 H) 8.14 (d, J=8.25 Hz, 2 H), and (600 MHz):0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.04 - 1.23 (m, 17 H) 1.28 (s, 3 H) 1.29 - 1.32 (m, 3 H) 1.44 - 1.67 (m, 3 H) 1.67 - 1.85 (m, 2 H) 2.06 - 2.45 (m, 6 H) 2.26 (s, 6 H) 2.33 (s, 3 H) 2.46 - 2.54 (m, 1 H) 2.57 - 2.66 (m, 1 H) 2.74 - 2.91 (m, 2 H) 3.13 - 3.42 (m, 4 H) 3.20 (s, 3 H) 3.32 (s, 3 H) 3.49 - 3.58 (m, 1 H) 3.67 (d, J=7.79 Hz, 1 H) 3.82 - 3.88 (m, 1 H) 4.15 - 4.25 (m, 1 H) 4.30 - 4.45 (m, 2 H) 4.48 - 4.53 (m, 1 H) 4.56 - 4.64 (m, 1 H) 4.95 (d, J=4.58 Hz, 1 H) 5.12 - 5.19 (m, 1 H) 7.44 (d, J=8.71 Hz, 2 H) 8.14 (d, J=8.25 Hz, 2 H)
313			939.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.25 (m, 17 H) 1.27 - 1.34 (m, 6 H) 1.47 - 1.69 (m, 3 H) 1.70 - 1.89 (m, 2 H) 2.11 - 2.46 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.66 (m, 3 H) 2.76 - 2.85 (m, 1 H) 2.85 - 2.94 (m, 1 H) 3.14 - 3.48 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.53 - 3.63 (m, 1 H) 3.66 - 3.74 (m, 2 H) 3.80 (s, 3 H) 4.21 (s, 1 H) 4.33 - 4.41 (m, 1 H) 4.41 - 4.48 (m, 1 H) 4.50 - 4.56 (m, 1 H) 4.63 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.19 - 5.30 (m, 1 H) 6.74 - 6.79 (m, 1 H) 6.81 (s, 1 H) 6.85 (d, J=7.34 Hz, 1 H) 7.19 - 7.24 (m, 1 H)
314			953.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.11 Hz, 3 H) 1.04 - 1.27 (m, 2 H) 1.05 - 1.20 (m, 18 H) 1.30 (s, 3 H) 1.37 - 1.41 (m, 3 H) 1.49 - 1.64 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.10 - 2.21 (m, 1 H) 2.20 - 2.46 (m, 4 H) 2.30 (s, 7 H) 2.36 (s, 3 H) 2.53 - 2.95 (m, 6 H) 3.14 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.55 - 3.66 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.10 - 4.22 (m, 2 H) 4.37 (s, 1 H) 4.42 - 4.55 (m, 2 H) 4.64 (s, 1 H) 4.96 (s, 1 H) 5.07 - 5.17 (m, 1 H) 6.72 - 6.82 (m, 2 H) 7.02 (t, J=6.19 Hz, 1 H) 7.15 (t, J=7.79 Hz, 1 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.11 Hz, 3 H) 1.04 - 1.27 (m, 2 H) 1.05 - 1.20 (m, 18 H) 1.30 (s, 3 H) 1.37 - 1.41 (m, 3 H) 1.49 - 1.64 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.10 - 2.21 (m, 1 H) 2.20 - 2.46 (m, 4 H) 2.30 (s, 7 H) 2.36 (s, 3 H) 2.53 - 2.95 (m, 6 H) 3.14 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.55 - 3.66 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.04 - 4.09 (m, 1 H) 4.14 - 4.21 (m, 1 H) 4.37 (s, 1 H) 4.42 - 4.55 (m, 2 H) 4.64 (s, 1 H) 4.96 (s, 1 H) 5.07 - 5.17 (m, 1 H) 6.72 - 6.82 (m, 2 H) 7.02 (t, J=6.19 Hz, 1 H) 7.15 (t, J=7.79 Hz, 1 H)

[0837] 

[Table 11-15]

315			953.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 (t, J=7.34 Hz, 3 H) 1.06 - 1.31 (m, 2 H) 1.08 - 1.31 (m, 18 H) 1.31 - 1.34 (m, 3 H) 1.48 - 1.88 (m, 5 H) 2.08 - 2.18 (m, 1 H) 2.21 - 2.51 (m, 7 H) 2.31 - 2.39 (m, 9 H) 2.55 - 2.76 (m, 2 H) 2.77 - 2.99 (m, 2 H) 3.19 - 3.24 (m, 3 H) 3.23 - 3.54 (m, 4 H) 3.39 - 3.42 (m, 3 H) 3.59 - 3.75 (m, 2 H) 3.92 (q, J=6.42 Hz, 1 H) 4.20 (s, 1 H) 4.32 - 4.42 (m, 1 H) 4.45 - 4.52 (m, 1 H) 4.58 (d, J=9.63 Hz, 1 H) 4.66 (s, 1 H) 4.96 - 5.02 (m, 1 H) 6.68 - 6.79 (m, 2 H) 6.98 (s, 1 H) 7.12 (t, J=7.79 Hz, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.01 (t, J=7.11 Hz, 3 H) 1.08 - 1.31 (m, 2 H) 1.08 - 1.31 (m, 18 H) 1.31 - 1.34 (m, 3 H) 1.48 - 1.88 (m, 5 H) 2.08 - 2.18 (m, 1 H) 2.21 - 2.51 (m, 7 H) 2.31 - 2.39 (m, 9 H) 2.55 - 2.76 (m, 2 H) 2.77 - 2.99 (m, 2 H) 3.19 - 3.24 (m, 3 H) 3.23 - 3.54 (m, 4 H) 3.39 - 3.42 (m, 3 H) 3.59 - 3.75 (m, 2 H) 3.92 (q, J=6.42 Hz, 1 H) 4.17 (s, 1 H) 4.32 - 4.42 (m, 1 H) 4.45 - 4.52 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.59 - 4.64 (m, 1 H) 4.96 - 5.02 (m, 1 H) 6.68 - 6.79 (m, 2 H) 7.07 (s, 1 H) 7.15 (t, J=7.79 Hz, 1 H)
316			925.6	mixture of diastereomers (600 MHz):0.75 - 0.82 (m, 6 H) 0.86 (t, J=7.34 Hz, 3 H) 1.00 - 1.17 (m, 14 H) 1.18 - 1.30 (m, 9 H) 1.43 - 1.66 (m, 3 H) 1.67 - 1.76 (m, 1 H) 1.77 - 1.86 (m, 1 H) 2.10 - 2.65 (m, 11 H) 2.30 (s, 6 H) 2.72 - 2.90 (m, 2 H) 3.12 - 3.46 (m, 4 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.50 - 3.69 (m, 3 H) 4.08 - 4.14 (m, 1 H) 4.23 - 4.31 (m, 1 H) 4.41 - 4.64 (m, 3 H) 4.91 (d, J=4.59 Hz, 1 H) 6.63 - 6.71 (m, 1 H) 6.71 - 6.79 (m, 1 H) 7.09 (d, J=8.71 Hz, 1 H) 7.13 (d, J=8.25 Hz, 1 H), and (600 MHz):0.75 - 0.82 (m, 6 H) 0.86 (t, J=7.34 Hz, 3 H) 1.00 - 1.17 (m, 14 H) 1.18 - 1.30 (m, 9 H) 1.43 - 1.66 (m, 3 H) 1.67 - 1.76 (m, 1 H) 1.77 - 1.86 (m, 1 H) 2.10 - 2.65 (m, 11 H) 2.31 (s, 6 H) 2.72 - 2.90 (m, 2 H) 3.12 - 3.46 (m, 4 H) 3.19 (s, 3 H) 3.37 (s, 3 H) 3.50 - 3.69 (m, 3 H) 4.02 - 4.08 (m, 1 H) 4.23 - 4.31 (m, 1 H) 4.41 - 4.64 (m, 3 H) 4.91 (d, J=4.59 Hz, 1 H) 6.63 - 6.71 (m, 1 H) 6.71 - 6.79 (m, 1 H) 7.09 (d, J=8.71 Hz, 1 H) 7.13 (d, J=8.25 Hz, 1 H)
317			952.7	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 (t, J=7.34 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.35 (d, J=6.88 Hz, 3 H) 1.48 - 1.90 (m, 5 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.53 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.70 (m, 4 H) 2.77 - 2.84 (m, 1 H) 2.89 (d, J=13.76 Hz, 1 H) 3.02 - 3.30 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.49 (m, 1 H) 3.49 - 3.59 (m, 1 H) 3.67 - 3.72 (m, 1 H) 3.93 - 4.02 (m, 1 H) 4.17 - 4.28 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.40 - 4.46 (m, 1 H) 4.49 (d, J=9.63 Hz, 1 H) 4.58 - 4.68 (m, 1 H) 4.74 - 4.83 (m, 1 H) 4.94 - 4.98 (m, 1 H) 6.60 (d, J=7.79 Hz, 1 H) 6.65 - 6.71 (m, 1 H) 7.02 - 7.08 (m, 2 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 (t, J=7.34 Hz, 3 H) 1.07 - 1.27 (m, 17 H) 1.30 (s, 3 H) 1.35 (d, J=6.88 Hz, 3 H) 1.48 - 1.90 (m, 5 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.53 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.70 (m, 4 H) 2.77 - 2.84 (m, 1 H) 2.89 (d, J=13.76 Hz, 1 H) 3.02 - 3.30 (m, 3 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.49 (m, 1 H) 3.49 - 3.59 (m, 1 H) 3.67 - 3.72 (m, 1 H) 3.93 - 4.02 (m, 1 H) 4.17 - 4.28 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.40 - 4.46 (m, 1 H) 4.49 (d, J=9.63 Hz, 1 H) 4.58 - 4.68 (m, 1 H) 4.93 - 5.02 (m, 2 H) 6.60 (d, J=7.79 Hz, 1 H) 6.65 - 6.71 (m, 1 H) 7.02 - 7.08 (m, 2 H)
318			982.7	mixture of diastereomers (600 MHz):0.81 (d, J=7.34 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 0.96 - 1.03 (m, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.36 (d, J=6.88 Hz, 3 H) 1.49 - 1.66 (m, 3 H) 1.70 - 1.90 (m, 2 H) 2.10 - 2.64 (m, 10 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.76 - 2.94 (m, 2 H) 3.18 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.35 (s, 3 H) 3.52 - 3.62 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.88 - 4.00 (m, 1 H) 4.19 - 4.29 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.51 - 4.57 (m, 1 H) 4.59 - 4.67 (m, 1 H) 4.94 - 5.00 (m, 1 H) 5.07 - 5.15 (m, 1 H) 7.50 (d, J=8.71 Hz, 2 H) 8.16 (d, J=7.34 Hz, 2 H)

[0838] 

[Table 11-16]

319			952.7	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.25 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.49 - 1.68 (m, 3 H) 1.70 - 1.79 (m, 1 H) 1.80 - 1.87 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.21 - 2.46 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.64 (m, 3 H) 2.77 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 2.92 (s, 6 H) 3.13 - 3.31 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.55 - 3.62 (m, 1 H) 3.62 - 3.68 (m, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.20 (s, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.59 - 4.68 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.23 - 5.31 (m, 1 H) 6.68 (d, J=8.71 Hz, 2 H) 7.12 (d, J=8.71 Hz, 2 H)
320			971.7	mixture of diastereomers (600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.11 Hz, 3 H) 0.94 (t, J=6.88 Hz, 3 H) 1.05 - 1.26 (m, 2 H) 1.09 - 1.20 (m, 15 H) 1.27 - 1.34 (m, 6 H) 1.48 - 1.68 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.12 - 2.49 (m, , 5 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.69 (m, 5 H) 2.77 - 2.84 (m, 1 H) 2.88 (s, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.61 (s, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.20 (s, 1 H) 4.28 - 4.36 (m, 1 H) 4.38 (s, 1 H) 4.47 (s, 1 H) 4.49 - 4.55 (m, 1 H) 4.64 (s, 1 H) 4.96 (s, 1 H) 5.19 - 5.30 (m, 1 H) 7.12 - 7.18 (m, 1 H) 7.19 - 7.24 (m, 1 H) 7.32 (d, J=7.79 Hz, 1 H) 7.39 - 7.45 (m, 1 H), and (600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.11 Hz, 3 H) 0.98 (t, J=7.11 Hz, 3 H) 1.05 - 1.26 (m, 2 H) 1.09 - 1.20 (m, 15 H) 1.27 - 1.34 (m, 6 H) 1.48 - 1.68 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.12 - 2.49 (m, , 5 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.69 (m, 5 H) 2.77 - 2.84 (m, 1 H) 2.88 (s, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.61 (s, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.20 (s, 1 H) 4.28 - 4.36 (m, 1 H) 4.38 (s, 1 H) 4.47 (s, 1 H) 4.49 - 4.55 (m, 1 H) 4.64 (s, 1 H) 4.96 (s, 1 H) 5.19 - 5.30 (m, 1 H) 7.12 - 7.18 (m, 1 H) 7.19 - 7.24 (m, 1 H) 7.32 (d, J=7.79 Hz, 1 H) 7.39 - 7.45 (m, 1 H)
321			967.8	mixture of diastereomers (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.95 - 1.04 (m, 3 H) 1.07 - 1.27 (m, 2 H) 1.10 - 1.21 (m, 15 H) 1.31 (s, 3 H) 1.32 (d, J=5.96 Hz, 3 H) 1.49 - 1.65 (m, 3 H) 1.70 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.21 - 2.53 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.65 (m, 3 H) 2.81 (dd, J=7.34, 5.50 Hz, 1 H) 2.85 - 2.93 (m, 1 H) 3.16 - 3.23 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.45 (m, 1 H) 3.55 - 3.63 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 3.80 (s, 3 H) 3.80 - 3.86 (m, 1 H) 4.21 (s, 1 H) 4.35 - 4.42 (m, 1 H) 4.46 (s, 1 H) 4.51 - 4.56 (m, 1 H) 4.64 (s, 1 H) 4.94 - 4.99 (m, 1 H) 5.20 (s, 1 H) 6.76 (d, J=7.79 Hz, 1 H) 6.83 (s, 1 H) 6.88 (d, J=7.79 Hz, 1 H) 7.21 (t, J=7.57 Hz, 1 H)
322			1073.7	(600 MHz):0.79 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.07 - 1.18 (m, 16 H) 1.19 - 1.27 (m, 1 H) 1.30 (s, 3 H) 1.38 (d, J=6.88 Hz, 3 H) 1.49 - 1.63 (m, J=15.13, 5.04 Hz, 2 H) 1.60 (dd, J=15.13, 5.04 Hz, 1 H) 1.70 - 1.88 (m, 2 H) 2.11 - 2.19 (m, 1 H) 2.29 (s, 6 H) 2.30 - 2.33 (m, 1 H) 2.36 (s, 3 H) 2.38 - 2.46 (m, 3 H) 2.49 - 2.64 (m, 6 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=11.92 Hz, 1 H) 3.16 - 3.30 (m, 2 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.39 (m, 1 H) 3.52 - 3.57 (m, 1 H) 3.71 (d, J=8.71 Hz, 1 H) 3.96 (q, J=6.72 Hz, 1 H) 4.21 - 4.30 (m, 1 H) 4.36 - 4.44 (m, 2 H) 4.55 (d, J=9.63 Hz, 1 H) 4.59 - 4.67 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.06 - 5.11 (m, 1 H) 7.75 (s, 1 H) 7.78 (s, 2 H)

[0839] 

[Table 11-17]

323			981.8	mixture of diastereomers (600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.92 - 1.00 (m, 3 H) 1.05 - 1.24 (m, 2 H) 1.10 - 1.19 (m, 15 H) 1.25 - 1.33 (m, 6 H) 1.38 - 1.43 (m, 3 H) 1.49 - 1.65 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.12 - 2.20 (m, 1 H) 2.21 - 2.32 (m, 2 H) 2.26 (s, 6 H) 2.33 - 2.65 (m, 7 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=16.05 Hz, 1 H) 3.15 - 3.27 (m, 3 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.46 (m, 1 H) 3.53 - 3.63 (m, 1 H) 3.69 - 3.74 (m, 1 H) 3.96 - 4.05 (m, 2 H) 4.22 (s, 1 H) 4.33 - 4.49 (m, 3 H) 4.50 - 4.56 (m, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.39 - 5.50 (m, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.86 - 6.93 (m, 1 H) 7.17 (t, J=7.11 Hz, 1 H) 7.27 (s, 1 H), and (600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.92 - 1.00 (m, 3 H) 1.05 - 1.24 (m, 2 H) 1.10 - 1.19 (m, 15 H) 1.25 - 1.33 (m, 6 H) 1.38 - 1.43 (m, 3 H) 1.49 - 1.65 (m, 3 H) 1.74 (s, 1 H) 1.84 (s, 1 H) 2.12 - 2.20 (m, 1 H) 2.21 - 2.32 (m, 2 H) 2.27 (s, 6 H) 2.33 - 2.65 (m, 7 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.88 (d, J=16.05 Hz, 1 H) 3.15 - 3.27 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.46 (m, 1 H) 3.53 - 3.63 (m, 1 H) 3.69 - 3.74 (m, 1 H) 4.04 - 4.13 (m, 2 H) 4.22 (s, 1 H) 4.33 - 4.49 (m, 3 H) 4.50 - 4.56 (m, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.39 - 5.50 (m, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.86 - 6.93 (m, 1 H) 7.17 (t, J=7.11 Hz, 1 H) 7.27 (s, 1 H)
324			967.8	(600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.98 (t, J=6.88 Hz, 3 H) 1.06 - 1.25 (m, 2 H) 1.13 (d, J=7.34 Hz, 3 H) 1.14 (s, 3 H) 1.15 - 1.18 (m, 6 H) 1.19 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.33 (d, J=6.88 Hz, 3 H) 1.50 - 1.68 (m, 3 H) 1.70 - 1.79 (m, 1 H) 1.80 - 1.88 (m, 1 H) 2.10 - 2.20 (m, 1 H) 2.22 - 2.34 (m, 2 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.52 (m, 4 H) 2.55 - 2.65 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.92 (m, 1 H) 3.16 - 3.25 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.56 - 3.65 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.76 - 3.84 (m, 1 H) 3.79 (s, 3 H) 4.21 (s, 1 H) 4.35 - 4.42 (m, 1 H) 4.47 (d, J=6.88 Hz, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.22 (s, 1 H) 6.76 (dd, J=7.79, 2.29 Hz, 1 H) 6.84 (s, 1 H) 6.88 (d, J=7.34 Hz, 1 H) 7.21 (t, J=8.02 Hz, 1 H)
325			1010.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.04 - 1.24 (m, 23 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.45 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.62 (m, 7 H) 2.78 - 2.91 (m, 2 H) 3.15 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.54 - 3.65 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 3.73 (s, 2 H) 4.18 - 4.23 (m, 1 H) 4.34 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.62 - 4,66 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.23 - 5.28 (m, 1 H) 6.71 - 6.73 (m, 1 H) 6.82 - 6.84 (m, 1 H) 7.01 - 7.03 (m, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.04 - 1.24 (m, 23 H) 1.28 (d, J=6.88 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.86 (m, 5 H) 2.10 - 2.45 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.54 - 2.62 (m, 7 H) 2.78 - 2.91 (m, 2 H) 3.15 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.54 - 3.65 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 3.73 (s, 2 H) 4.18 - 4.23 (m, 1 H) 4.34 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.62 - 4.66 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.23 - 5.28 (m, 1 H) 6.71 - 6.73 (m, 1 H) 6.82 - 6.84 (m, 1 H) 7.01 - 7.03 (m, 1 H)

[0840] 

[Table 11-18]

326			1022.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08-1.25 (m, 17 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.88 (m, 11 H) 2.11 - 2.63 (m, 12 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.14 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.55 - 3.62 (m, 2 H) 3.63 (s, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.19 - 4.23 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.96 - 4.99 (m, 1 H) 5.23 - 5.26 (m, 1 H) 6.72 - 6.74 (m, 1 H) 6.82 - 6.83 (m, 1 H) 7.01 - 7.04 (m, 1 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08- 1.25 (m, 17 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.88 (m, 11 H) 2.11 - 2.63 (m, 12 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.14 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.55 - 3.62 (m, 2 H) 3.63 (s, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.19 - 4.23 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.96 - 4.99 (m, 1 H) 5.23 - 5.26 (m, 1 H) 6.72 - 6.74 (m, 1 H) 6.82 - 6.83 (m, 1 H) 7.01 - 7.04 (m, 1 H)
327			1036.8	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06-1.26 (m, 17 H) 1.28 - 1.32 (m, 6 H) 1.37 - 1.86 (m, 11 H) 2.10 - 2.46 (m, 9 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.53 - 2.61 (m, 3 H) 2.77 - 2.92 (m, 2 H) 3.12 - 3.61 (m, 7 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.65 - 3.72 (m, 2 H) 3.78 (s, 3 H) 4.19 - 4.23 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.41 - 4.45 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.60 - 4.67 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.25 - 5.32 (m, 1 H) 6.77 - 6.81 (m, 1 H) 7.07 - 7.13 (m, 1 H) 7.21 - 7.24 (m, 1 H)
328			1038.8	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07-1.25 (m, 17 H) 1.28 - 1.32 (m, 6 H) 1.50 - 1.86 (m, 5 H) 2.10 - 2.62 (m, 12 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.79 - 2.84 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.53 (s, 3 H) 3.54 - 3.60 (m, 1 H) 3.66 - 3.73 (m, 6 H) 3.80 (s, 2 H) 4.20 - 4.24 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.54 (d, J=10.09 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.23 - 5.29 (m, 1 H) 6.79 - 6.83 (m, 1 H) 7.11 - 7.14 (m, 1 H) 7.20 - 7.22 (m, 1 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07- 1.25 (m, 17 H) 1.28 - 1.32 (m, 6 H) 1.50 - 1.86 (m, 5 H) 2.10 - 2.62 (m, 12 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.79 - 2.84 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.53 (s, 3 H) 3.54 - 3.60 (m, 1 H) 3.66 - 3.73 (m, 6 H) 3.80 (s, 2 H) 4.20 - 4.24 (m, 1 H) 4.35 - 4.40 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.54 (d, J=10.09 Hz, 1 H) 4.60 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.23 - 5.29 (m, 1 H) 6.79 - 6.83 (m, 1 H) 7.11 - 7.14 (m, 1 H) 7.20 - 7.22 (m, 1 H)

[0841] 

[Table 11-19]

329			1010.8	mixture of diastereomers (600 MHz): 0.84 (d, J=6.88 Hz, 6 H) 0.92 (t, J=7.34 Hz, 3 H) 1.10 - 1.27 (m, 17 H) 1.31 (d, J=6.42 Hz, 3 H) 1.33 (s, 3 H) 1.53 - 1.90 (m, 5 H) 2.13 - 2.48 (m, 5 H) 2.32 (s, 6 H) 2.38 (s, 3 H) 2.55 - 2.66 (m, 3 H) 2.80 - 2.86 (m, 1 H) 2.88 - 2.93 (m, 1 H) 3.00 (s, 3 H) 3.10 (s, 3 H) 3.17 - 3.49 (m, 4 H) 3.26 (s, 3 H) 3.36 (s, 3 H) 3.57 - 3.64 (m, 1 H) 3.68 - 3.74 (m, 2 H) 4.22 - 4.25 (m, 1 H) 4.37 - 4.42 (m, 1 H) 4.45 - 4.49 (m, 1 H) 4.54 - 4.58 (m, 1 H) 4.64 - 4.69 (m, 3 H) 4.99 (d, J=4.58 Hz, 1 H) 5.23 - 5.28 (m, 1 H) 6.88 - 6.92 (m, 2 H) 7.17 - 7.22 (m, 2 H), and (600 MHz):0.84 (d, J=6.88 Hz, 6 H) 0.92 (t, J=7.34 Hz, 3 H) 1.10 - 1.27 (m, 17 H) 1.31 (d, J=6.88 Hz, 3 H) 1.33 (s, 3 H) 1.53 - 1.90 (m, 5 H) 2.13 - 2.48 (m, 5 H) 2.32 (s, 6 H) 2.38 (s, 3 H) 2.55 - 2.66 (m, 3 H) 2.80 - 2.86 (m, 1 H) 2.88 - 2.93 (m, 1 H) 3.00 (s, 3 H) 3.10 (s, 3 H) 3.17 - 3.49 (m, 4 H) 3.26 (s, 3 H) 3.36 (s, 3 H) 3.57 - 3.64 (m, 1 H) 3.68 - 3.74 (m, 2 H) 4.22 - 4.25 (m, 1 H) 4.37 - 4.42 (m, 1 H) 4.45 - 4.49 (m, 1 H) 4.54 - 4.58 (m, 1 H) 4.64 - 4.69 (m, 3 H) 4.99 (d, J=4.58 Hz, 1 H) 5.23 - 5.28 (m, 1 H) 6.88 - 6.92 (m, 2 H) 7.17 - 7.22 (m, 2 H)
330			1052.7	mixture of diastereomers (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07-1.25 (m, 17 H) 1.30 (s, 6 H) 1.49 - 1.88 (m, 5 H) 2.10 - 2.46 (m, 5 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.62 (m, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.15 - 3.46 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.55 - 3.72 (m, 11 H) 4.18 - 4.23 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.51 - 4.55 (m, 1 H) 4.61 - 4.67 (m, 3 H) 4.97 (d, J=4.13 Hz, 1 H) 5.20 - 5.25 (m, 1 H) 6.85 - 6.90 (m, 2 H) 7.17 - 7.20 (m, 2 H)
331			1007.8	mixture of diastereomers (600 MHz): 0.82 (d, J=5.96 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.07-1.25 (m, 17 H) 1.28 - 1.31 (m, 6 H) 1.50 - 1.88 (m, 5 H) 2.12 - 2.47 (m, 5 H) 2.30 (s, 6 H) 2.34 (s, 3 H) 2.35 (s, 3 H) 2.53 - 2.63 (m, 7 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.14 - 3.52 (m, 14 H) 3.56 - 3.62 (m, 1 H) 3.63 - 3.69 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.18 - 4.22 (m, 1 H) 4.34 - 4.40 (m, 1 H) 4.43 - 4.48 (m, 1 H) 4.53 (d, J=10.55 Hz, 1 H) 4.62 - 4.67 (m, 1 H) 4.95 - 4.98 (m, 1 H) 5.21 - 5.26 (m, 1 H) 6.87 (d, J=8.71 Hz, 2 H) 7.14 (d, J=8.25 Hz, 2 H)
332			1038.8	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.93 - 1.01 (m, 3 H) 1.05 - 1.25 (m, 23 H) 1.27 - 1.33 (m, 6 H) 1.50 - 1.88 (m, 5 H) 2.11 - 2.66 (m, 14 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.79 - 2.83 (m, 1 H) 2.85 - 2.92 (m, 1 H) 3.15 - 3.79 (m, 9 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 4.20 - 4.25 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.44 - 4.48 (m, 1 H) 4.52 - 4.56 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.22 - 5.25 (m, 1 H) 6.72 (d, J=8.25 Hz, 1 H) 6.84 (br. s., 1 H) 7.05 (d, J=8.25 Hz, 1 H)
333			1050.9	mixture of diastereomers (600 MHz):0.84 (d, J=6.88 Hz, 6 H) 0.92 (t, J=7.34 Hz, 3 H) 0.95 - 1.05 (m, 3 H) 1.10-1.28 (m, 17 H) 1.29 - 1.35 (m, 6 H) 1.49 - 1.91 (m, 11 H) 2.14 - 2.65 (m, 14 H) 2.31 (s, 6 H) 2.38 (s, 3 H) 2.81 - 2.87 (m, 1 H) 2.88 - 2.95 (m, 1 H) 3.17 - 3.50 (m, 4 H) 3.25 (s, 3 H) 3.37 (s, 3 H) 3.59 - 3.82 (m, 5 H) 4.23 - 4.27 (m, 1 H) 4.40 - 4.45 (m, 1 H) 4.47 - 4.51 (m, 1 H) 4.54 - 4.60 (m, 1 H) 4.64 - 4.69 (m, 1 H) 5.00 (d, J=4.59 Hz, 1 H) 5.24 - 5.27 (m, 1 H) 6.74 - 6.76 (m, 1 H) 6.84 - 6.87 (m, 1 H) 7.06 - 7.10 (m, 1 H)

[0842] 

[Table 11-20]

334			1064.9	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.95 - 1.01 (m, 3 H) 1.07 - 1.25 (m, 17 H) 1.28 - 1.34 (m, 6 H) 1.37 - 1.87 (m, 11 H) 2.10 - 2.64 (m, 14 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.78 - 2.83 (m, 1 H) 2.86 - 2.92 (m, 1 H) 3.15 - 3.24 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.36 - 3.61 (m, 4 H) 3.71 (d, J=8.25 Hz, 1 H) 3.77 - 3.86 (m, 4 H) 4.21 - 4.26 (m, 1 H) 4.37 - 4.47 (m, 2 H) 4.53 - 4.57 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 5.31 - 5.38 (m, 1 H) 6.78 (d, J=8.25 Hz, 1 H) 7.08 - 7.13 (m, 1 H) 7.26 - 7.29 (m, 1 H)
335			1066.9	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.95 - 1.01 (m, 3 H) 1.07 - 1.25 (m, 17 H) 1.28 - 1.35 (m, 6 H) 1.50 - 1.87 (m, 5 H) 2.10 - 2.51 (m, 11 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.64 (m, 3 H) 2.78 - 2.84 (m, 1 H) 2.86 - 2.91 (m, 1 H) 3.16 - 3.24 (m, 3 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.45 (m, 1 H) 3.52 - 3.60 (m, 1 H) 3.54 (s, 2 H) 3.67 - 3.73 (m, 5 H) 3.77 - 3.85 (m, 4 H) 4.21 - 4.27 (m, 1 H) 4.36 - 4.47 (m, 2 H) 4.53 - 4.56 (m, 1 H) 4.61 - 4.66 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.27 - 5.33 (m, 1 H) 6.80 (d, J=8.25 Hz, 1 H) 7.11 - 7.16 (m, 1 H) 7.23 - 7.26 (m, 1 H)
336			1038.8	mixture of diastereomers (600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.94 - 1.01 (m, 3 H) 1.07 - 1.26 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.50 - 1.88 (m, 5 H) 2.12 - 2.47 (m, 7 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.62 (m, 3 H) 2.77 - 2.92 (m, 2 H) 2.98 (s, 3 H) 3.08 (s, 3 H) 3.16 - 3.23 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.56 - 3.64 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.76 - 3.84 (m, 1 H) 4.19 - 4.24 (m, 1 H) 4.36 - 4.42 (m, 1 H) 4.44 - 4.48 (m, 1 H) 4.52 - 4.55 (m, 1 H) 4.62 - 4.65 (m, 1 H) 4.65 (s, 2 H) 4.95 - 4.99 (m, 1 H) 5.19 - 5.24 (m, 1 H) 6.87 (d, J=8.25 Hz, 2 H) 7.19 (d, J=8.25 Hz, 2 H)
337			1080.9	mixture of diastereomers (600 MHz):0.77 (d, J=6.88 Hz, 6 H) 0.85 (t, J=7.34 Hz, 3 H) 0.89 - 0.96 (m, 3 H) 1.03 - 1.21 (m, 17 H) 1.24 - 1.28 (m, 6 H) 1.45 - 1.83 (m, 5 H) 2.09 - 2.43 (m, 7 H) 2.24 (s, 6 H) 2.31 (s, 3 H) 2.47 - 2.57 (m, 3 H) 2.74 - 2.79 (m, 1 H) 2.82 - 2.86 (m, 1 H) 3.13 - 3.18 (m, 3 H) 3.19 (s, 3 H) 3.30 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.53 - 3.63 (m, 9 H) 3.67 (d, J=7.79 Hz, 1 H) 3.72 - 3.80 (m, 1 H) 4.16 - 4.20 (m, 1 H) 4.32 - 4.37 (m, 1 H) 4.40 - 4.43 (m, 1 H) 4.48 - 4.51 (m, 1 H) 4.57 - 4.63 (m, 3 H) 4.92 - 4.94 (m, 1 H) 5.15 - 5.19 (m, 1 H) 6.82 (d, J=8.25 Hz, 2 H) 7.16 (d, J=8.25 Hz, 2 H)

[0843] 

[Table 11-21]

338			1035.9	mixture of diastereomers (600 MHz):0.77 (d, J=6.88 Hz, 6 H) 0.85 (t, J=7.34 Hz, 3 H) 0.89 - 0.96 (m, 3 H) 1.03 - 1.21 (m, 17 H) 1.24 - 1.28 (m, 6 H) 1.45 - 1.83 (m, 5 H) 2.09 - 2.43 (m, 7 H) 2.24 (s, 6 H) 2.31 (s, 3 H) 2.47 - 2.57 (m, 3 H) 2.74 - 2.79 (m, 1 H) 2.82 - 2.86 (m, 1 H) 3.13 - 3.18 (m, 3 H) 3.19 (s, 3 H) 3.30 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.53 - 3.63 (m, 9 H) 3.67 (d, J=7.79 Hz, 1 H) 3.72 - 3.80 (m, 1 H) 4.16 - 4.20 (m, 1 H) 4.32 - 4.37 (m, 1 H) 4.40 - 4.43 (m, 1 H) 4.48 - 4.51 (m, 1 H) 4.57 - 4.63 (m, 3 H) 4.92 - 4.94 (m, 1 H) 5.15 - 5.19 (m, 1 H) 6.82 (d, J=8.25 Hz, 2 H) 7.16 (d, J=8.25 Hz, 2 H)
339			1002.7	mixture of diastereomers (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.26 (m, 2 H) 1.09 - 1.19 (m, 15 H) 1.28 - 1.35 (m, 6 H) 1.50 - 1.58 (m, 1 H) 1.57 - 1.63 (m, 1 H) 1.68 - 1.80 (m, 2 H) 1.83 (s, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.32 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.59 (m, 1 H) 2.59 - 2.72 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.89 (d, J=14.21 Hz, 1 H) 3.00 (s, 3 H) 3.15 - 3.28 (m, 3 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.47 (m, 1 H) 3.57 (s, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.74 (q, J=6.72 Hz, 1 H) 4.17 - 4.26 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.50 - 4.55 (m, 1 H) 4.63 (s, 1 H) 4.94 - 4.99 (m, 1 H) 5.19 - 5.26 (m, 1 H) 7.06 - 7.14 (m, 2 H) 7.18 (s, 1 H) 7.26 - 7.31 (m, 1 H), and (600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 -1.26 (m, 2 H) 1.09 - 1.19 (m, 15 H) 1.28 - 1.35 (m, 6 H) 1.50 - 1.58 (m, 1 H) 1.57 - 1.63 (m, 1 H) 1.68 - 1.80 (m, 2 H) 1.83 (s, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.32 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.59 (m, 1 H) 2.59 - 2.72 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.89 (d, J=14.21 Hz, 1 H) 3.01 (s, 3 H) 3.15 - 3.28 (m, 3 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.35 - 3.47 (m, 1 H) 3.57 (s, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 3.74 (q, J=6.72 Hz, 1 H) 4.17 - 4.26 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.50 - 4.55 (m, 1 H) 4.63 (s, 1 H) 4.94 - 4.99 (m, 1 H) 5.25 - 5.31 (m, 1 H) 7.06 - 7.14 (m, 2 H) 7.18 (s, 1 H) 7.26 - 7.31 (m, 1 H)
340			1002.7	mixture of diastereomers (600 MHz):0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.04 - 1.24 (m, 2 H) 1.07 - 1.19 (m, 15 H) 1.28 (s, 3 H) 1.29 - 1.34 (m, 3 H) 1.48 - 1.56 (m, 1 H) 1.56 - 1.61 (m, 1 H) 1.60 - 1.87 (m, 3 H) 2.07 - 2.18 (m, 1 H) 2.19 - 2.45 (m, 4 H) 2.30 (s, 6 H) 2.34 (s, 3 H) 2.49 - 2.67 (m, 3 H) 2.75 - 2.82 (m, 1 H) 2.83 - 2.90 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.20 (s, 3 H) 3.31 (s, 3 H) 3.50 - 3.59 (m, 1 H) 3.68 (d, J=8.25 Hz, 1 H) 3.77 - 3.85 (m, 1 H) 4.20 (s, 1 H) 4.32 - 4.39 (m, 1 H) 4.39 - 4.44 (m, 1 H) 4.50 - 4.54 (m, 1 H) 4.60 (s, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 5.16 - 5.23 (m, 1 H) 6.47 (d, J=7.79 Hz, 2 H) 7.24 - 7.28 (m, 2 H) 7.39 - 7.45 (m, 2 H) 7.54 (d, J=7.79 Hz, 2 H), and (600 MHz):0.79 (d, J=6.88 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.04 - 1.24 (m, 2 H) 1.07 - 1.19 (m, 15 H) 1.28 (s, 3 H) 1.29 - 1.34 (m, 3 H) 1.48 - 1.56 (m, 1 H) 1.56 - 1.61 (m, 1 H) 1.60 - 1.87 (m, 3 H) 2.07 - 2.18 (m, 1 H) 2.19 - 2.45 (m, 4 H) 2.30 (s, 6 H) 2.34 (s, 3 H) 2.49 - 2.67 (m, 3 H) 2.75 - 2.82 (m, 1 H) 2.83 - 2.90 (m, 1 H) 3.13 - 3.45 (m, 4 H) 3.20 (s, 3 H) 3.32 (s, 3 H) 3.50 - 3.59 (m, 1 H) 3.68 (d, J=8.25 Hz, 1 H) 3.77 - 3.85 (m, 1 H) 4.20 (s, 1 H) 4.32 - 4.39 (m, 1 H) 4.39 - 4.44 (m, 1 H) 4.50 - 4.54 (m, 1 H) 4.60 (s, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 5.16 - 5.23 (m, 1 H) 6.47 (d, J=7.79 Hz, 2 H) 7.24 - 7.28 (m, 2 H) 7.39 - 7.45 (m, 2 H) 7.54 (d, J=7.79 Hz, 2 H)

[0844] 

[Table 11-22]

341			1008.8	mixture of diastereomers (500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.45 Hz, 3 H) 1.04 - 1.26 (m, 2 H) 1.07 - 1.21 (m, 15 H) 1.27 - 1.34 (m, 6 H) 1.47 - 1.79 (m, 6 H) 1.79 - 1.89 (m, 1 H) 1.92 - 2.03 (m, 2 H) 2.08 - 2.47 (m, 5 H) 2.31 (s, 6 H) 2.35 (s, 3 H) 2.52 - 2.68 (m, 3 H) 2.75 - 2.83 (m, 1 H) 2.83 - 2.92 (m, 3 H) 3.12 - 3.45 (m, 4 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.47 - 3.55 (m, 2 H) 3.54 - 3.62 (m, 1 H) 3.63 - 3.72 (m, 2 H) 3.76 - 3.85 (m, 1 H) 4.17 (s, 1 H) 4.31 - 4.40 (m, 1 H) 4.41 - 4.47 (m, 1 H) 4.48 - 4.53 (m, 1 H) 4.63 (s, 1 H) 4.95 (d, J=4.59 Hz, 1 H) 5.36 - 5.45 (m, 1 H) 6.86 (d, J=8.79 Hz, 2 H) 7.13 (d, J=8.79 Hz, 2 H)
342			1031.7	mixture of diastereomers (500 MHz):0.82 (d, J=7.20 Hz, 6 H) 0.90 (t, J=7.20 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.66 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.10 - 2.20 (m, 1 H) 2.22 - 2.46 (m, 4 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.48 - 2.70 (m, 3 H) 2.77 - 2.94 (m, 2 H) 2.83 (s, 6 H) 3.12 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.52 - 3.63 (m, 1 H) 3.67 - 3.76 (m, 2 H) 4.13 - 4.28 (m, 1 H) 4.33 - 4.49 (m, 2 H) 4.50 - 4.56 (m, 1 H) 4.59 - 4.68 (m, 1 H) 4.94 - 4.99 (m, 1 H) 5.22 - 5.31 (m, 1 H) 6.98 - 7.27 (m, 4 H), and (500 MHz): 0.82 (d, J=7.20 Hz, 6 H) 0.90 (t, J=7.20 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.28 - 1.33 (m, 6 H) 1.48 - 1.66 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.10 - 2.20 (m, 1 H) 2.22 - 2.46 (m, 4 H) 2.31 (s, 6 H) 2.36 (s, 3 H) 2.48 - 2.70 (m, 3 H) 2.77 - 2.94 (m, 2 H) 2.84 (s, 6 H) 3.12 - 3.48 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.52 - 3.63 (m, 1 H) 3.67 - 3.76 (m, 2 H) 4.13 - 4.28 (m, 1 H) 4.33 - 4.49 (m, 2 H) 4.50 - 4.56 (m, 1 H) 4.59 - 4.68 (m, 1 H) 4.94 - 4.99 (m, 1 H) 5.22 - 5.31 (m, 1 H) 6.98 - 7.27 (m, 4 H)
343			1030.7	mixture of diastereomers (500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.26 Hz, 3 H) 0.95 - 1.03 (m, 3 H) 1.05 - 1.27 (m, 2 H) 1.10 - 1.19 (m, 15 H) 1.29 - 1.34 (m, 6 H) 1.50 - 1.58 (m, 1 H) 1.57 - 1.64 (m, 1 H) 1.64 - 1.90 (m, 3 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.33 (s, 6 H) 2.36 (s, 3 H) 2.44 - 2.65 (m, 4 H) 2.66 - 2.76 (m, 1 H) 2.76 - 2.85 (m, 1 H) 2.90 (d, J=14.91 Hz, 1 H) 3.00 (s, 3 H) 3.05 - 3.44 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.62 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.84 (q, J=6.75 Hz, 1 H) 4.24 (s, 1 H) 4.36 - 4.45 (m, 1 H) 4.47 (d, J=7.26 Hz, 1 H) 4.50 - 4.56 (m, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.20 - 5.26 (m, 1 H) 7.09 (d, J=7.26 Hz, 1 H) 7.15 (t, J=7.26 Hz, 1 H) 7.26 (t, J=7.45 Hz, 1 H) 7.32 (d, J=13.00 Hz, 1 H), and (500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t J=7.26 Hz, 3 H) 0.95 - 1.03 (m, 3 H) 1.05 - 1.27 (m, 2 H) 1.10 - 1.19 (m, 15 H) 1.29 - 1.34 (m, 6 H) 1.50 - 1.58 (m, 1 H) 1.57 - 1.64 (m, 1 H) 1.64 - 1.90 (m, 3 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.33 (s, 6 H) 2.36 (s, 3 H) 2.44 - 2.65 (m, 4 H) 2.66 - 2.76 (m, 1 H) 2.76 - 2.85 (m, 1 H) 2.90 (d, J=14.91 Hz, 1 H) 3.00 (s, 3 H) 3.13 - 3.42 (m, 4 H) 3.22 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.62 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.84 (q, J=6.75 Hz, 1 H) 4.24 (s, 1 H) 4.36 - 4.45 (m, 1 H) 4.47 (d, J=7.26 Hz, 1 H) 4.50 - 4.56 (m, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.25 - 5.31 (m, 1 H) 7.09 (d, J=7.26 Hz, 1 H) 7.15 (t, J=7.26 Hz, 1 H) 7.26 (t, J=7.45 Hz, 1 H) 7.32 (d, J=13.00 Hz, 1 H)

[0845] 

[Table 11-23]

344			1030.8	mixture of diastereomers (500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 0.95 - 1.05 (m, 3 H) 1.06 - 1.27 (m, 2 H) 1.10 (s, 3 H) 1.12 (d, J=6.50 Hz, 3 H) 1.14 - 1.21 (m, 9 H) 1.29 (s, 3 H) 1.36 (d, J=4.97 Hz, 3 H) 1.49 - 1.63 (m, 2 H) 1.63 - 1.70 (m, 1 H) 1.70 - 1.79 (m, 1 H) 1.79 - 1.89 (m, 1 H) 2.11 - 2.20 (m, 1 H) 2.20 - 2.68 (m, 9 H) 2.31 (s, 6 H) 2.35 (s, 3 H) 2.76 - 2.84 (m, 1 H) 2.88 (d, J=15.29 Hz, 1 H) 3.19 - 3.27 (m, 3 H) 3.21 (s, 3 H) 3.31 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.53 - 3.61 (m, 1 H) 3.69 (d, J=8.03 Hz, 1 H) 3.90 - 3.96 (m, 1 H) 4.21 (s, 1 H) 4.33 - 4.42 (m, 1 H) 4.44 (d, J=6.50 Hz, 1 H) 4.52 (d, J=9.94 Hz, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.20 Hz, 1 H) 5.17 - 5.28 (m, 1 H) 6.49 (d, J=7.64 Hz, 2 H) 7.23 - 7.30 (m, 2 H) 7.47 (d, J=8.79 Hz, 2 H) 7.58 (d, J=7.65 Hz, 2 H), and (500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 0.95 - 1.05 (m, 3 H) 1.06 - 1.27 (m, 2 H) 1.10 (s, 3 H) 1.12 (d, J=6.50 Hz, 3 H) 1.14 - 1.21 (m, 9 H) 1.29 (s, 3 H) 1.36 (d, J=4.97 Hz, 3 H) 1.49 - 1.63 (m, 2 H) 1.63 - 1.70 (m, 1 H) 1.70 - 1.79 (m, 1 H) 1.79 - 1.89 (m, 1 H) 2.11 - 2.20 (m, 1 H) 220 - 2.68 (m, 9 H) 2.31 (s, 6 H) 2.35 (s, 3 H) 2.76 - 2.84 (m, 1 H) 2.88 (d, J=15.29 Hz, 1 H) 3.19 - 3.27 (m, 3 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.53 - 3.61 (m, 1 H) 3.69 (d, J=8.03 Hz, 1 H) 3.86 - 3.91 (m, 1 H) 4.21 (s, 1 H) 4.33 - 4.42 (m, 1 H) 4.44 (d, J=6.50 Hz, 1 H) 4.53 (d, J=9.56 Hz, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.20 Hz, 1 H) 5.17 - 5.28 (m, 1 H) 6.49 (d, J=7.64 Hz, 2 H) 7.23 - 7.30 (m, 2 H) 7.46 (d, J=8.41 Hz, 2 H) 7.58 (d, J=7.65 Hz, 2 H)
345			1036.8	mixture of diastereomers (500 MHz): 0.81 (d, J=6.50 Hz, 6 H) 0.89 (t, J=7.26 Hz, 3 H) 0.94 - 1.02 (m, 3 H) 1.07 - 1.26 (m, 2 H) 1.10 - 1.21 (m, 15 H) 1.26 - 1.35 (m, 6 H) 1.46 - 1.79 (m, 6 H) 1.79 - 1.90 (m, 1 H) 1.93 - 2.02 (m, 2 H) 2.11 - 2.20 (m, 1 H) 2.21 - 2.49 (m, 6 H) 2.28 - 2.31 (m, 6 H) 2.35 (s, 3 H) 2.51 - 2.66 (m, 3 H) 2.76 - 2.84 (m, 1 H) 2.84 - 2.92 (m, 3 H) 3.14 - 3.26 (m, 3 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.48 - 3.56 (m, 2 H) 3.55 - 3.64 (m, 1 H) 3.70 (d, J=7.64 Hz, 1 H) 3.74 - 3.86 (m, 2 H) 4.19 (s, 1 H) 4.33 - 4.41 (m, 1 H) 4.43 - 4.49 (m, 1 H) 4.52 (d, J=9.56 Hz, 1 H) 4.64 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 5.33 (s, 1 H) 6.86 (d, J=8.41 Hz, 2 H) 7.14 (d, J=8.41 Hz, 2 H)
346			1027.8	mixture of diastereomer (500 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.45 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.27 - 1.32 (m, 6 H) 1.48 - 1.90 (m, 5 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.47 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.49 - 2.65 (m, 4 H) 2.77 - 2.85 (m, 1 H) 2.89 (d, J=14.91 Hz, 1 H) 3.02 - 3.06 (m, 1 H) 3.14 - 3.45 (m, 4 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.53 - 3.63 (m, 1 H) 3.66 - 3.73 (m, 2 H) 4.21 (s, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.50 - 4.57 (m, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.21 - 5.28 (m, 1 H) 6.95 (d, J=8.41 Hz, 2 H) 7.16 (d, J=8.41 Hz, 2 H) 7.29 (d, J=6.12 Hz, 2 H) 8.56 (d, J=5.73 Hz, 2 H)

[0846] 

[Table 11-24]

347			1059.8	mixture of diastereomers (500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 0.94 - 1.03 (m, 3 H) 1.04 - 1.26 (m, 2 H) 1.11 - 1.19 (m, 15 H) 1.26 - 1.34 (m, 6 H) 1.48 - 1.69 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.78 - 1.87 (m, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.71 (m, 9 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.85 (m, 1 H) 2.82 (s, 6 H) 2.88 (d, J=15.29 Hz, 1 H) 3.04 - 3.40 (m, 4 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.54 - 3.61 (m, 1 H) 3.71 (d, J=8.41 Hz, 1 H) 3.77 - 3.87 (m, 1 H) 4.26 (s, 1 H) 4.38 - 4.50 (m, 2 H) 4.50 - 4.56 (m, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.20 Hz, 1 H) 5.28 - 5.35 (m, 1 H) 6.98 - 7.11 (m, 2 H) 7.18 - 7.25 (m, 1 H) 7.29 (d, J=14.14 Hz, 1 H), and (500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 0.94 - 1.03 (m, 3 H) 1.04 - 1.26 (m, 2 H) 1.11 - 1.19 (m, 15 H) 1.26 - 1.34 (m, 6 H) 1.48 - 1.69 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.78 - 1.87 (m, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.71 (m, 9 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.85 (m, 1 H) 2.82 (s, 6 H) 2.88 (d, J=15.29 Hz, 1 H) 3.10 - 3.42 (m, 4 H) 3.21 (s, 3 H) 3.33 (s, 3 H) 3.54 - 3.61 (m, 1 H) 3.71 (d, J=8.41 Hz, 1 H) 3.77 - 3.87 (m, 1 H) 4.26 (s, 1 H) 4.38 - 4.50 (m, 2 H) 4.50 - 4.56 (m, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.20 Hz, 1 H) 5.22 - 5.28 (m, 1 H) 6.98 - 7.11 (m, 2 H) 7.18 - 7.25 (m, 1 H) 7.29 (d, J=14.14 Hz, 1 H)
348			913.7	mixture of diastereomers (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.09 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.34 (d, J=6.88 Hz, 3 H) 1.51 - 1.88 (m, 5 H) 2.13 - 2.46 (m, 5 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.55 - 2.61 (m, 1 H) 2.66 - 2.70 (m, 2 H) 2.79 - 2.84 (m, 1 H) 2.87 - 2.92 (m, 1 H) 3.18 - 3.36 (m, 6 H) 3.23 (s, 3 H) 3.37 - 3.42 (m, 1 H) 3.54 - 3.62 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.74 - 3.79 (m, 1 H) 3.86 (s, 3 H) 4.19 - 4.24 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.62 - 4.67 (m, 1 H) 4.98 (d, J=4.58 Hz, 1 H) 5.26 - 5.30 (m, 1 H) 7.24 (s, 1 H) 7.37 (s, 1 H), and (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.09 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.33 (d, J=6.88 Hz, 3 H) 1.51 - 1.88 (m, 5 H) 2.13 - 2.46 (m, 5 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.55 - 2.61 (m, 1 H) 2.66 - 2.70 (m, 2 H) 2.79 - 2.84 (m, 1 H) 2.87 - 2.92 (m, 1 H) 3.18 - 3.36 (m, 6 H) 3.23 (s, 3 H) 3.37 - 3.42 (m, 1 H) 3.54 - 3.62 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.74 - 3.79 (m, 1 H) 3.86 (s, 3 H) 4.19 - 4.24 (m, 1 H) 4.35 - 4.41 (m, 1 H) 4.42 - 4.46 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.62 - 4.67 (m, 1 H) 4.98 (d, J=4.58 Hz, 1 H) 5.26 - 5.30 (m, 1 H) 7.24 (s, 1 H) 7.37 (s, 1 H)
349			988.7	mixture of diastereomers (600 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 (d, J=5.96 Hz, 3 H) 1.07 - 1.26 (m, 14 H) 1.30 - 1.34 (m, 6 H) 1.51 - 1.88 (m, 5 H) 2.10 - 2.84 (m, 18 H) 2.87 - 2.93 (m, 1 H) 3.18 - 3.34 (m, 9 H) 3.37 - 3.44 (m, 1 H) 3.53 - 3.61 (m, 1 H) 3.68 - 3.72 (m, 1 H) 3.81 - 3.86 (m, 1 H) 4.19 - 4.22 (m, 1 H) 4.34 - 4.46 (m, 2 H) 4.52 - 4.56 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.94 - 4.99 (m, 1 H) 5.32 - 5.41 (m, 1 H) 7.44 (d, J=8.25 Hz, 2 H) 7.83 - 7.87 (m, 2 H), and (600 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.03 (d, J=5.96 Hz, 3 H) 1.07 - 1.26 (m, 14 H) 1.30 - 1.34 (m, 6 H) 1.51 - 1.88 (m, 5 H) 2.10 - 2.84 (m, 18 H) 2.87 - 2.93 (m, 1 H) 3.18 - 3.34 (m, 9 H) 3.37 - 3.44 (m, 1 H) 3.53 - 3.61 (m, 1 H) 3.68 - 3.72 (m, 1 H) 3.81 - 3.86 (m, 1 H) 4.19 - 4.22 (m, 1 H) 4.34 - 4.46 (m, 2 H) 4.52 - 4.56 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.94 - 4.99 (m, 1 H) 5.32 - 5.41 (m, 1 H) 7.44 (d, J=8.25 Hz, 2 H) 7.83 - 7.87 (m, 2 H)

[0847] 

[Table 11-25]

350			941.7	mixture of diastereomers (600 MHz):0.83 (d, J=6.88 Hz, 6 H) 0.91 (t, J=7.11 Hz, 3 H) 1.04 - 1.37 (m, 20 H) 1.44 (d, J=6.42 Hz, 3 H) 1.52 - 1.90 (m, 5 H) 2.13 - 2.45 (m, 5 H) 2.43 (s, 6 H) 2.53 (s, 3 H) 2.55 - 2.98 (m, 5 H) 3.08 - 3.51 (m, 10 H) 3.60 - 3.72 (m, 2 H) 3.78 - 3.99 (m, 1 H) 4.04 - 4.18 (m, 1 H) 4.30 - 4.39 (m, 1 H) 4.46 - 4.55 (m, 2 H) 4.60 - 4.67 (m, 1 H) 4.88 - 4.92 (m, 1 H) 4.97 - 5.00 (m, 1 H) 6.11 - 6.32 (m, 2 H) 6.79 (d, J=8.25 Hz, 1 H), and (600 MHz):0.83 (d, J=6.88 Hz, 6 H) 0.91 (t, J=7.11 Hz, 3 H) 1.04 - 1.37 (m, 20 H) 1.42 (d, J=6.42 Hz, 3 H) 1.52 - 1.90 (m, 5 H) 2.13 - 2.45 (m, 5 H) 2.43 (s, 6 H) 2.53 (s, 3 H) 2.55 - 2.98 (m, 5 H) 3.08 - 3.51 (m, 10 H) 3.60 - 3.72 (m, 2 H) 3.78 - 3.99 (m, 1 H) 4.04 - 4.18 (m, 1 H) 4.30 - 4.39 (m, 1 H) 4.46 - 4.55 (m, 2 H) 4.60 - 4.67 (m, 1 H) 4.88 - 4.92 (m, 1 H) 4.97 - 5.00 (m, 1 H) 6.11 - 6.32 (m, 2 H) 6.79 (d, J=8.25 Hz, 1 H)
351			941.8	mixture of diastereomers (600 MHz):0.82 (d, J=5.96 Hz, 6 H) 0.89 - 0.93 (m, 3 H) 1.05 - 1.22 (m, 16 H) 1.23 - 1.34 (m, 7 H) 1.50 - 1.89 (m, 5 H) 2.11 - 3.03 (m, 10 H) 2.38 (s, 6 H) 2.45 (s, 3 H) 3.15 - 3.55 (m, 4 H) 3.22 (s, 3 H) 3.38 (s, 3 H) 3.57 - 3.66 (m, 2 H) 3.69 (d, J=7.79 Hz, 1 H) 4.11 - 4.18 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.47 - 4.56 (m, 2 H) 4.59 - 4.66 (m, 1 H) 4.95 - 4.99 (m, 1 H) 5.04 - 5.08 (m, 1 H) 6.24 - 6.28 (m, 1 H) 6.33 - 6.37 (m, 2 H), and (600 MHz): 0.82 (d, J=5.96 Hz, 6 H) 0.89 - 0.93 (m, 3 H) 1.05 - 1.22 (m, 16 H) 1.23 - 1.34 (m, 7 H) 1.50 - 1.89 (m, 5 H) 2.11 - 3.03 (m, 10 H) 2.38 (s, 6 H) 2.45 (s, 3 H) 3.15 - 3.55 (m, 4 H) 3.22 (s, 3 H) 3.36 (s, 3 H) 3.57 - 3.66 (m, 2 H) 3.69 (d, J=7.79 Hz, 1 H) 4.11 - 4.18 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.47 - 4.56 (m, 2 H) 4.59 - 4.66 (m, 1 H) 4.95 - 4.99 (m, 1 H) 5.44 - 5.49 (m, 1 H) 6.24 - 6.28 (m, 1 H) 6.33 - 6.37 (m, 2 H)
352			939.7	(600 MHz):0.91 (d, J=6.88 Hz, 6 H) 0.99 (t, J=7.34 Hz, 3 H) 1.16 - 1.32 (m, 2 H) 1.22 (d, J=6.88 Hz, 3 H) 1.24 - 1.29 (m, 12 H) 1.40 (s, 3 H) 1.42 (d, J=6.88 Hz, 3 H) 1.58 - 1.74 (m, 3 H) 1.79 - 1.88 (m, 1 H) 1.90 - 1.97 (m, 1 H) 2.21 - 2.30 (m, 1 H) 2.30 - 2.56 (m, 4 H) 2.38 (s, 6 H) 2.45 (s, 3 H) 2.61 - 2.71 (m, 3 H) 2.87 - 2.94 (m, 1 H) 2.98 (d, J=14.67 Hz, 1 H) 3.25 - 3.40 (m, 3 H) 3.33 (s, 3 H) 3.43 (s, 3 H) 3.50 (s, 1 H) 3.63 - 3.71 (m, 1 H) 3.80 (d, J=8.25 Hz, 1 H) 3.91 (s, 3 H) 4.15 (q, J=6.72 Hz, 1 H) 4.30 (s, 1 H) 4.43 - 4.51 (m, 1 H) 4.54 (d, J=6.88 Hz, 1 H) 4.63 (d, J=9.63 Hz, 1 H) 4.74 (s, 1 H) 5.07 (d, J=4.59 Hz, 1 H) 5.41 - 5.47 (m, 1 H) 6.95 (d, J=8.25 Hz, 1 H) 7.01 (t, J=7.57 Hz, 1 H) 7.27 - 7.34 (m, 2 H)

[0848] 

[Table 11-26]

353			937.8	mixture of diastereomers (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 - 1.26 (m, 2 H) 1.12 (d, J=7.34 Hz, 3 H) 1.13 - 1.21 (m, 12 H) 1.21 - 1.24 (m, 3 H) 1.31 (s, 3 H) 1.31 - 1.34 (m, 3 H) 1.50 - 1.68 (m, 3 H) 1.70 - 1.80 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.47 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.64 (m, 3 H) 2.63 (q, J=7.79 Hz, 2 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=17.42 Hz, 1 H) 3.15 - 3.45 (m, 4 H) 3.22 - 3.24 (m, 3 H) 3.33 (s, 3 H) 3.53 - 3.63 (m, 1 H) 3.66 - 3.74 (m, 2 H) 4.17 - 4.26 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.23 - 5.30 (m, 1 H) 7.05 - 7.10 (m, 3 H) 7.19 - 7.24 (m, 1 H), and (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 - 1.26 (m,, 2 H) 1.12 (d, J=7.34 Hz, 3 H) 1.13 - 1.21 (m, 12 H) 1.21 - 1.24 (m, 3 H) 1.31 (s, 3 H) 1.31 - 1.34 (m, 3 H) 1.50 - 1.68 (m, 3 H) 1.70 - 1.80 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.47 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.53 - 2.64 (m, 3 H) 2.63 (q, J=7.79 Hz, 2 H) 2.77 - 2.84 (m, 1 H) 2.88 (d, J=17.42 Hz, 1 H) 3.15 - 3.45 (m, 4 H) 3.22 - 3.24 (m, 3 H) 3.34 (s, 3 H) 3.53 - 3.63 (m, 1 H) 3.66 - 3.74 (m, 2 H) 4.17 - 4.26 (m, 1 H) 4.34 - 4.41 (m, 1 H) 4.42 - 4.47 (m, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.23 - 5.30 (m, 1 H) 7.05 - 7.1 (m, 3 H) 7.19 - 7.24 (m, 1 H)
354			1036.8	mixture of diastereomers (600 MHz):0.78 - 0.86 (m, 6 H) 0.90 (t, J=7.57 Hz, 3 H) 1.06 - 1.26 (m" 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 - 1.20 (m, 12 H) 1.28 (s, 3 H) 1.36 (d, J=6.42 Hz, 3 H) 1.50 - 1.68 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.90 (m, 1 H) 2.12 - 2.47 (m, 5 H) 2.27 (s, 6 H) 2.35 (s, 3 H) 2.48 - 2.66 (m, 2 H) 2.69 - 2.93 (m, 3 H) 3.20 - 3.36 (m" 3 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.56 (s, 1 H) 3.70 (d, J=9.17 Hz, 1 H) 3.81 - 3.88 (m, 1 H) 4.19 (s, 1 H) 4.33 - 4.40 (m, 1 H) 4.43 (d, J=6.42 Hz, 1 H) 4.54 (d, J=10.09 Hz, 1 H) 4.63 (s, 1 H) 4.72 (s, 2 H) 4.93 - 4.98 (m, 1 H) 4.94 (s, 2 H) 5.24 - 5.27 (m, 1 H) 7.44 - 7.51 (m, 2 H) 7.54 - 7.60 (m, 2 H), and (600 MHz):0.78 - 0.86 (m, 6 H) 0.90 (t, J=7.57 Hz, 3 H) 1.06 - 1.26 (m" 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 - 1.20 (m, 12 H) 1.29 (s, 3 H) 1.36 (d, J=6.42 Hz, 3 H) 1.50 - 1.68 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.80 - 1.90 (m, 1 H) 2.12 - 2.47 (m, 5 H) 2.30 (s, 6 H) 2.34 (s, 3 H) 2.48 - 2.66 (m, 2 H) 2.69 - 2.93 (m, 3 H) 3.20 - 3.36 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.56 (s, 1 H) 3.70 (d, J=9.17 Hz, 1 H) 3.81 - 3.88 (m, 1 H) 4.19 (s, 1 H) 4.33 - 4.40 (m, 1 H) 4.43 (d, J=6.42 Hz, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.63 (s, 1 H) 4.72 (s, 2 H) 4.92 (s, 2 H) 4.93 - 4.98 (m, 1 H) 5.27 - 5.31 (m, 1 H) 7.44 - 7.51 (m, 2 H) 7.57 (m, 2 H)
355			925.8	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 - 1.23 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.13 (d, J=5.96 Hz, 3 H) 1.15 - 1.19 (m, 9 H) 1.29 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.58 (m, 1 H) 1.63 (dd, J=15.36, 4.81 Hz, 1 H) 1.68 (d, J=12.38 Hz, 1 H) 1.72 - 1.79 (m, 1 H) 1.80 - 1.87 (m, 1 H) 2.11 - 2.19 (m, 1 H) 2.19 - 2.26 (m, 1 H) 2.29 - 2.52 (m, 4 H) 2.37 (s, 3 H) 2.40 (s, 6 H) 2.74 - 2.85 (m, 2 H) 2.85 - 3.00 (m, 2 H) 3.00 - 3.08 (m, 1 H) 3.22 (s, 3 H) 3.30 - 3.35 (m, 1 H) 3.35 - 3.47 (m, 2 H) 3.36 (s, 3 H) 3.58 - 3.65 (m, 1 H) 3.66 - 3.73 (m, 2 H) 4.14 (s, 1 H) 4.32 - 4.39 (m, 1 H) 4.49 (d, J=7.34 Hz, 1 H) 4.53 (d, J=10.09 Hz, 1 H) 4.62 (s, 1 H) 4.97 (d, J=4.58 Hz, 1 H) 5.07 (s, 1 H) 6.67 - 6.74 (m, 2 H) 6.90 (s, 1 H) 7.13 (t, J=7.79 Hz, 1 H)

[0849] 

[Table 11-27]

356			965.9	mixture of diastereomers (600 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.00 (t, J=7.11 Hz, 3 H) 1.06 - 1.27 (m, 2 H) 1.11 - 1.15 (m, 6 H) 1.15 - 1.21 (m, 9 H) 1.21 - 1.24 (m, 3 H) 1.31 (s, 3 H) 1.33 (d, J=6.88 Hz, 3 H) 1.50 - 1.67 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.81 - 1.89 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.23 - 2.51 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.55 - 2.65 (m, 3 H) 2.63 (q, J=7.79 Hz, 2 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.17 - 3.25 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.59 (s, 1 H) 3.72 (d, J=8.25 Hz, 1 H) 3.82 - 3.87 (m, 1 H) 4.22 (s, 1 H) 4.36 - 4.43 (m, 1 H) 4.43 - 4.49 (m, 1 H) 4.53 (d, J=9.63 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.19 - 5.28 (m, 1 H) 7.04 - 7.12 (m, 3 H) 7.21 (t, J=7.57 Hz, 1 H), and (600 MHz): 0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.97 (t, J=7.57 Hz, 3 H) 1.06 - 1.27 (m, 2 H) 1.11 - 1.15 (m, 6 H) 1.15- 1.21 (m, 9 H) 1.21 - 1.24 (m, 3 H) 1.31 (s, 3 H) 1.34 (d, J=6.88 Hz, 3 H) 1.50 - 1.67 (m, 3 H) 1.69 - 1.79 (m, 1 H) 1.81 - 1.89 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.23 - 2.51 (m, 6 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.55 - 2.65 (m, 3 H) 2.63 (q, J=7.79 Hz, 2 H) 2.78 - 2.84 (m, 1 H) 2.85 - 2.93 (m, 1 H) 3.17 - 3.25 (m, 3 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.59 (s, 1 H) 3.72 (d, J=8.25 Hz, 1 H) 3.76 - 3.82 (m, 1 H) 4.22 (s, 1 H) 4.36 - 4.43 (m, 1 H) 4.43 - 4.49 (m, 1 H) 4.54 (d, J=9.63 Hz, 1 H) 4.64 (s, 1 H) 4.97 (d, J=4.59 Hz, 1 H) 5.19 - 5.28 (m, 1 H) 7.04 - 7.12 (m, 3 H) 7.21 (t, J=7.57 Hz, 1 H)
357			985.9	mixture of diastereomers (500 MHz):0.81 (d, J=6.58 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.05 - 1.34 (m, 23 H) 1.50 - 1.89 (m, 4 H) 2.11 - 2.45 (m, 15 H) 2.48 - 2.73 (m, 3 H) 2.76 - 2.93 (m, 2 H) 3.13 - 3.43 (m, 10 H) 3.50 - 3.61 (m, 1 H) 3.62 - 3.72 (m, 2 H) 3.88 (s, 6 H) 4.16 - 4.24 (m, 1 H) 4.30 - 4.69 (m, 4 H) 4.94 - 4.99 (m, 1 H) 5.10 - 5.32 (m, 1 H) 6.50 - 6.54 (m, 2 H)
358			833.9	(500 MHz):0.78 - 0.86 (m, 6 H) 0.86 - 0.93 (m, 3 H) 1.04 - 1.28 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.90 (m, 6 H) 2.05 - 2.12 (m, 1 H) 2.1 - 2.58 (m, 8 H) 2.21 (s, 6 H) 2.30 (s, 7 H) 2.77 - 2.96 (m, 2 H) 3.16 - 3.34 (m, 3 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.52 (m, 2 H) 3.64 - 3.68 (m, 1 H) 4.09 - 4.16 (m, 1 H) 4.40 - 4.47 (m, 1 H) 4.51 (s, 1 H) 4.53 - 4.69 (m, 2 H) 5.03 - 5.07 (m, 1 H) 5.37 - 5.43 (m, 1 H)
359			806.8	(500 MHz):0.79 - 0.86 (m, 6 H) 0.89 (t, J=7.26 Hz, 3 H) 1.05 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.89 (m, 5 H) 2.08 - 2.13 (m, 1 H) 2.20 - 2.34 (m, 8 H) 2.36 (s, 3 H) 2.40 - 2.56 (m, 2 H) 2.78 - 2.94 (m, 2 H) 3.22 - 3.25 (m, 4 H) 3.32 (s, 3 H) 3.34 - 3.51 (m, 5 H) 3.65 (d, J=7.26 Hz, 1 H) 3.73 (t, J=5.16 Hz, 2 H) 4.10 - 4.16 (m, 1 H) 4.41 - 4.47 (m, 1 H) 4.52 (s, 1 H) 4.54 - 4.68 (m, 2 H) 5.05 (d, J=4.97 Hz, 1 H) 5.24 - 5.32 (m, 1 H)

[0850] 

[Table 11-28]

360			982.0	(500 MHz):0.77 - 0.86 (m, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 (s, 3 H) 1.07 - 1.12 (m, 1 H) 1.07 - 1.11 (m, 3 H) 1.13 (d, J=6.58 Hz, 3 H) 1.15 - 1.19 (m, 1 H) 1.18 (d, J=6.03 Hz, 3 H) 1.19 (s, 3 H) 1.22 - 1.28 (m, 6 H) 1.31 (s, 3 H) 1.45 - 1.69 (m, 5 H) 1.70 - 1.79 (m, 1 H) 1.81 - 1.90 (m, 1 H) 2.08 (d, J=15.36 Hz, 1 H) 2.14 - 2.30 (m, 3 H) 2.27 (s, 6 H) 2.35 (s, 3 H) 2.39 - 2.55 (m, 5 H) 2.57 - 2.64 (m, 1 H) 2.71 - 2.78 (m, 1 H) 2.79 - 2.84 (m, 1 H) 2.89 (d, J=15.36 Hz, 1 H) 3.19 (dd, J=10.28, 7.27 Hz, 1 H) 3.22 - 3.28 (m, 1 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.44 - 3.51 (m, 1 H) 3.67 (d, J=7.68 Hz, 1 H) 3.81 (s, 3 H) 4.09 - 4.17 (m, 1 H) 4.37 - 4.43 (m, 1 H) 4.45 (d, J=6.86 Hz, 1 H) 4.48 (s, 1 H) 4.50 - 4.56 (m, 1 H) 4.61 - 4.70 (m, 1 H) 5.02 (d, J=4.39 Hz, 1 H) 6.11 - 6.18 (m, 1 H) 6.85 (d, J=8.23 Hz, 1 H) 6.93 (t, J=7.27 Hz, 1 H) 7.18 - 7.23 (m, 1 H) 7.30 (d, J=7.68 Hz, 1 H)
361			968.0	(500 MHz):0.77 - 0.86 (m, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 0.94 (t, J=7.13 Hz, 3 H) 1.08 (s, 3 H) 1.08 - 1.18 (m, 2 H) 1.10 (d, J=7.40 Hz, 3 H) 1.12 (d, J=6.58 Hz, 3 H) 1.18 (d, J=6.31 Hz, 6 H) 1.28 (d, J=6.86 Hz, 3 H) 1.31 (s, 3 H) 1.52 - 1.68 (m, 3 H) 1.69 - 1.78 (m, 1 H) 1.80 - 1.90 (m, 1 H) 2.09 (d, J=14.81 Hz, 1 H) 2.14 - 2.21 (m, 1 H) 2.22 - 2.32 (m, 2 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.40 - 2.61 (m, 6 H) 2.78 - 2.86 (m, 1 H) 2.90 (d, J=12.34 Hz, 1 H) 3.16 - 3.25 (m, 3 H) 3.25 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.50 (m, 2 H) 3.66 (d, J=7.68 Hz, 1 H) 3.84 (s, 3 H) 4.09 - 4.15 (m, 1 H) 4.35 (q, J=6.86 Hz, 1 H) 4.44 (d, J=7.40 Hz, 1 H) 4.50 (s, 1 H) 4.51 - 4.57 (m, 1 H) 4.60 - 4.70 (m, 1 H) 5.04 (d, J=4.94 Hz, 1 H) 5.65 - 5.69 (m, 1 H) 6.87 (d, J=7.95 Hz, 1 H) 6.91 (t, J=7.54 Hz, 1 H) 7.17 - 7.22 (m, 1 H) 7.26 - 7.30 (m, 1 H)
362			748.4	(600 MHz):0.78 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.14 (m, 1 H) 1.13 - 1.18 (m, 6 H) 1.18 (s, 3 H) 1.23 (d, J=5.96 Hz, 3 H) 1.24 - 1.29 (m, 2 H) 1.31 (s, 3 H) 1.47 - 1.58 (m, 1 H) 1.68 - 1.82 (m, 2 H) 1.85 (dd, J=15.13, 5.04 Hz, 1 H) 2.05 (d, J=15.13 Hz, 1 H) 2.10 - 2.19 (m, 1 H) 2.20 - 2.47 (m, 13 H) 2.53 - 2.63 (m, 1 H) 2.75 - 2.81 (m, 1 H) 2.87 - 2.96 (m, 2 H) 3.19 (d, J=10.09 Hz, 1 H) 3.22 (s, 3 H) 3.23 - 3.26 (m, 1 H) 3.27 (s, 3 H) 3.36 (s, 3 H) 3.37 - 3.41 (m, 1 H) 3.42 - 3.48 (m, 1 H) 3.59 (d, J=10.09 Hz, 1 H) 3.70 (d, J=7.79 Hz, 1 H) 4.15 - 4.21 (m, 1 H) 4.35 - 4.40 (m, 2 H) 4.56 - 4.65 (m, 1 H) 4.97 (d, J=4.58 Hz, 1 H)
363			748.4	(600 MHz):0.73 - 0.79 (m, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.05 (d, J=7.34 Hz, 3 H) 1.06 - 1.08 (m, 1 H) 1.09 (s, 3 H) 1.09 - 1.12 (m, 6 H) 1.16 (d, J=6.42 Hz, 3 H) 1.17 - 1.23 (m, 1 H) 1.27 (s, 3 H) 1.44 - 1.53 (m, 1 H) 1.58 - 1.78 (m, 3 H) 1.81 (dd, J=15.13, 5.04 Hz, 1 H) 2.00 (d, J=15.13 Hz, 1 H) 2.07 - 2.15 (m, 1 H) 2.18 - 2.26 (m, 2 H) 2.27 (s, 6 H) 2.31 (s, 3 H) 2.34 - 2.42 (m, 1 H) 2.45 - 2.54 (m, 1 H) 2.58 (d, J=13.76 Hz, 1 H) 2.71 - 2.77 (m, 1 H) 2.81 - 2.87 (m, 1 H) 2.89 (d, J=13.76 Hz, 1 H) 3.12 - 3.19 (m, 1 H) 3.18 (s, 3 H) 3.23 (s, 3 H) 3.30 - 3.38 (m, 1 H) 3.41 - 3.49 (m, 1 H) 3.65 (d, J=8.25 Hz, 1 H) 4.11 - 4.19 (m, 1 H) 4.33 (d, J=7.34 Hz, 1 H) 4.35 - 4.42 (m, 1 H) 4.52 - 4.62 (m, 1 H) 4.93 (d, J=5.04 Hz, 1 H)

[0851] 

[Table 11-29]

364			762.5	(600 MHz):0.79 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.08 (d, J=6.88 Hz, 3 H) 1.10 - 1.12 (m, 1 H) 1.14 (d, J=7.34 Hz, 3 H) 1.18 (s, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.24 (s, 3 H) 1.26 - 1.30 (m, 1 H) 1.33 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.66 - 1.81 (m, 2 H) 1.83 (dd, J=14.90, 4.81 Hz, 1 H) 2.03 (d, J=15.13 Hz, 1 H) 2.11 - 2.31 (m, 3 H) 2.33 - 2.56 (m, 16 H) 2.63 - 2.83 (m, 3 H) 2.91 (d, J=15.13 Hz, 1 H) 3.21 (s, 3 H) 3.23 - 3.28 (m, 1 H) 3.30 (s, 3 H) 3.36 - 3.42 (m, 1 H) 3.62 - 3.70 (m, 2 H) 4.14 - 4.22 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.48 - 4.65 (m, 2 H) 4.93 (d, J=4.59 Hz, 1 H)
365			776.1	(600 MHz):0.77 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.07 (d, J=7.79 Hz, 3 H) 1.09 (s, 3 H) 1.09 - 1.11 (m, 1 H) 1.11 - 1.17 (m, 6 H) 1.21 (d, J=5.96 Hz, 3 H) 1.23 - 1.27 (m, 1 H) 1.30 (s, 3 H) 1.48 - 1.56 (m, 1 H) 1.61 - 1.84 (m, 3 H) 1.88 (dd, J=14.67, 5.04 Hz, 1 H) 1.97 (d, J=14.67 Hz, 1 H) 2.05 (d, J=15.13 Hz, 1 H) 2.10 - 2.20 (m, 1 H) 2.20 - 2.29 (m, 2 H) 2.31 (s, 6 H) 2.34 (s, 9 H) 2.38 - 2.56 (m, 2 H) 2.73 (d, J=14.67 Hz, 1 H) 2.75 - 2.79 (m, 1 H) 2.89 (d, J=15.59 Hz, 1 H) 3.19 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.34 - 3.46 (m, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.12 - 4.20 (m, 2 H) 4.36 (d, J=6.88 Hz, 1 H) 4.61 (br. s., 1 H) 4.97 (d, J=5.04 Hz, 1 H)
366			790.4	(600 MHz):0.78 - 0.83 (m, 6 H) 0.90 (t, J=7.57 Hz, 3 H) 1.07 (d, J=7.34 Hz, 3 H) 1.12 - 1.17 (m, 7 H) 1.18 - 1.25 (m, 7 H) 1.30 (s, 3 H) 1.50 - 1.59 (m, 1 H) 1.63 - 1.84 (m, 3 H) 1.88 (dd, J=15.13, 5.04 Hz, 1 H) 2.09 - 2.16 (m, 1 H) 2.20 (d, J=15.13 Hz, 1 H) 2.22 - 2.27 (m, 1 H) 2.27 - 2.33 (m, 7 H) 2.36 (s, 3 H) 2.38 - 2.53 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.85 - 2.92 (m, 1 H) 3.17 - 3.23 (m, 2 H) 3.20 (s, 3 H) 3.30 (s, 3 H) 3.31 - 3.37 (m, 2 H) 3.63 (d, J=4.13 Hz, 1 H) 3.88 (d, J=10.55 Hz, 1 H) 4.25 - 4.29 (m, 1 H) 4.30 (d, J=7.34 Hz, 1 H) 4.38 (q, J=6.72 Hz, 1 H) 4.56 - 4.66 (m, 1 H) 5.00 (d, J=4.59 Hz, 1 H)
367			779.5	(600 MHz):0.77 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.04 - 1.09 (m, 1 H) 1.09 (d, J=7.34 Hz, 3 H) 1.11 - 1.17 (m, 10 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 - 1.26 (m, 1 H) 1.31 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.59 - 1.83 (m, 3 H) 1.84 (dd, J=15.13, 5.50 Hz, 1 H) 2.04 - 2.08 (m, 1 H) 2.09 (s, 3 H) 2.11 - 2.19 (m, 1 H) 2.23 - 2.32 (m, 8 H) 2.36 (s, 3 H) 2.38 - 2.46 (m, 1 H) 2.47 - 2.55 (m, 1 H) 2.62 (d, J=14.21 Hz, 1 H) 2.75 - 2.81 (m, 1 H) 2.83 (d, J=14.67 Hz, 1 H) 2.90 (d, J=15.13 Hz, 1 H) 3.09 (s, 1 H) 3.17 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.46 - 3.55 (m, 1 H) 3.66 (d, J=8.25 Hz, 1 H) 4.13 - 4.24 (m, 1 H) 4.37 (d, J=7.34 Hz, 1 H) 4.44 (q, J=6.42 Hz, 1 H) 4.54 - 4.66 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H)
368				(600 MHz):0.79 (d, J=6.42 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.03 - 1.26 (m, 2 H) 1.07 (d, J=7.34 Hz, 3 H) 1.10 (s, 3 H) 1.11 (d, J=6.42 Hz, 3 H) 1.13 (d, J=7.34 Hz, 3 H) 1.18 (d, J=5.96 Hz, 3 H) 1.29 (s, 3 H) 1.46 - 1.56 (m, 1 H) 1.56 - 1.88 (m, 6 H) 2.02 (d, J=14.67 Hz, 1 H) 2.07 - 2.18 (m, 1 H) 2.20 - 2.50 (m, 11 H) 2.26 (s, 6 H) 2.33 (s, 3 H) 2.59 - 2.67 (m, 2 H) 2.71 - 2.80 (m, 2 H) 2.83 - 2.91 (m, 1 H) 3.14 - 3.22 (m, 1 H) 3.20 (s, 3 H) 3.25 (s, 3 H) 3.33 - 3.43 (m, 1 H) 3.46 - 3.54 (m, 1 H) 3.62 - 3.71 (m, 5 H) 4.17 (s, 1 H) 4.30 - 4.38 (m, 2 H) 4.59 (s, 1 H) 4.94 (d, J=4.59 Hz, 1 H)

[0852] 

[Table 11-30]

369			911.9	mixture of diastereomers (600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.91 (t, J=7.34 Hz, 3 H) 1.07 (d, J=7.34 Hz, 3 H) 1.08 - 1.40 (m, 17 H) 1.12 (d, J=5.96 Hz, 3 H) 1.52 - 1.58 (m, 1 H) 1.59 - 1.67 (m, 1 H) 1.72 - 1.88 (m, 3 H) 2.01 - 2.08 (m, 1 H) 2.10 - 2.33 (m, 3 H) 2.34 - 2.70 (m, 16 H) 2.72 - 2.83 (m, 2 H) 2.90 - 2.96 (m, 1 H) 3.18 - 3.32 (m, 6 H) 3.32 - 3.39 (m, 1 H) 3.39 - 3.60 (m, 2 H) 3.62 - 3.77 (m, 3 H) 4.12 - 4.20 (m, 1 H) 4.36 (d, J=6.88 Hz, 1 H) 4.40 - 4.48 (m, 1 H) 4.57 - 4.65 (m, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 6.64 - 6.82 (m, 3 H) 7.13 - 7.21 (m, 1 H)
370			819.8	(500 MHz):0.81 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.09 (d, J=7.13 Hz, 3 H) 1.11 - 1.17 (m, 1 H) 1.12 (s, 3H) 1.13 - 1.17 (m, 6 H) 1.20 (d, J=6.31 Hz, 3 H) 1.21 - 1.26 (m, 1 H) 1.31 (s, 3 H) 1.48 - 1.57 (m, 1 H) 1.60 - 1.66 (m, 1 H) 1.68 - 1.79 (m, 1 H) 1.79 - 1.90 (m, 2 H) 2.01 - 2.06 (m, 1 H) 2.11 - 2.18 (m, 1 H) 2.18 - 2.53 (m, 7 H) 2.21 (s, 6 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.64 - 2.94 (m, 5 H) 3.16 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.35 - 3.56 (m, 2 H) 3.70 (d, J=8.23 Hz, 1 H) 4.14 - 4.23 (m, 1 H) 4.29 - 4.41 (m, 2 H) 4.53 - 4.67 (m, 1 H) 4.96 (d, J=4.39 Hz, 1 H)
371			792.8	(500 MHz):0.81 (d, J=6.86 Hz, 6 H) 0.86 - 0.92 (m, 3 H) 1.04 - 1.36 (m, 20 H) 1.38 - 1.47 (m, 2 H) 1.48 - 1.89 (m, 5 H) 2.04 (d, J=14.81 Hz, 1 H) 2.10 - 2.53 (m, 6 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.54 - 2.60 (m, 2 H) 2.73 - 2.94 (m, 3 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.35 - 3.45 (m, 1 H) 3.51 - 3.60 (m, 1 H) 3.70 (d, J=7.95 Hz, 1 H) 4.14 - 4.22 (m, 1 H) 4.34 - 4.42 (m, 2 H) 4.56 - 4.67 (m, 1 H) 4.96 (d, J=4.66 Hz, 1 H)
372			804.8	(500 MHz):0.76 - 0.84 (m, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.05 - 1.30 (m, 20 H) 1.34 (s, 3 H) 1.48 - 1.87 (m, 5 H) 2.03 - 2.18 (m, 2 H) 2.20 - 2.45 (m, 4 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.59 (m, 1 H) 2.62 - 2.69 (m, 2 H) 2.75 - 2.82 (m, 3 H) 2.87 - 2.94 (m, 1 H) 3.19 - 3.30 (m, 1 H) 3.21 (s, 3 H) 3.28 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.51 - 3.71 (m, 5 H) 4.18 - 4.25 (m, 1 H) 4.38 (d, J=6.58 Hz, 1 H) 4.51 - 4.65 (m, 2 H) 4.96 (d, J=4.66 Hz, 1 H)
373			911.9	(600 MHz):0.86 (d, J=6.88 Hz, 6 H) 0.95 (t, J=7.34 Hz, 3 H) 1.06 - 1.33 (m, 17 H) 1.35 (s, 3 H) 1.36 (d, J=6.88 Hz, 3 H) 1.55 - 1.63 (m, 1 H) 1.65 - 1.70 (m, 1 H) 1.75 - 1.93 (m, 3 H) 2.09 (d, J=14.67 Hz, 1 H) 2.15 - 2.38 (m, 3 H) 2.39 - 2.75 (m, 8 H) 2.41 (s, 3 H) 2.45 (s, 6 H) 2.79 - 2.87 (m, 1 H) 2.93 - 3.03 (m, 1 H) 3.26 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.52 (m, 2 H) 3.59 - 3.66 (m, 1 H) 3.72 (d, J=7.79 Hz, 1 H) 3.77 (q, J=6.57 Hz, 1 H) 4.15 - 4.21 (m, 1 H) 4.40 (d, J=6.88 Hz, 1 H) 4.46 - 4.53 (m, 1 H) 4.62 - 4.69 (m, 1 H) 4.99 (d, J=5.04 Hz, 1 H) 6.72 - 6.77 (m, 1 H) 6.80 - 6.87 (m, 2 H) 7.20 (t, J=7.79 Hz, 1 H)

[0853] 

[Table 11-31]

374			943.9	(600 MHz):0.79 - 0.83 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.09 (s, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.10 - 1.31 (m, 2 H) 1.15 (d, J=7.79 Hz, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.23 (d, J=6.42 Hz, 3 H) 1.36 (s, 3 H) 1.50 - 1.85 (m, 5 H) 2.05 (d, J=15.13 Hz, 1 H) 2.10 - 2.17 (m, 1 H) 2.23 - 2.44 (m, 2 H) 2.27 (s, 6 H) 2.37 (s, 3 H) 2.57 - 2.63 (m, 3 H) 2.75 - 2.93 (m, 4 H) 3.20 (s, 3 H) 3.21 (s, 3 H) 3.30 (dd, J=9.86, 6.65 Hz, 1 H) 3.35 - 3.39 (m, 1 H) 3.45 (dd, J=11.23, 2.98 Hz, 1 H) 3.47 - 3.51 (m, 1 H) 3.52 - 3.58 (m, 1 H) 3.66 (d, J=8.25 Hz, 1 H) 3.69 (dd, J=11.46, 4.13 Hz, 1 H) 4.23 - 4.26 (m, 1 H) 4.37 (d, J=6.42 Hz, 1 H) 4.57 - 4.62 (m, 1 H) 4.64 - 4.69 (m, 1 H) 4.86 (d, J=5.96 Hz, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 7.57 (d, J=8.25 Hz, 2 H) 8.20 (d, J=8.71 Hz, 2 H)
375				(600 MHz):0.78 - 0.83 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.17 - 1.27 (m, 2 H) 1.20 (s, 3 H) 1.21 - 1.23 (m, 6 H) 1.35 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.63 - 1.69 (m, 1 H) 1.71 - 1.88 (m, 3 H) 2.08 (d, J=15.13 Hz, 1 H) 2.09 - 2.17 (m, 1 H) 2.22 - 2.45 (m, 3 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.49 - 2.55 (m, 1 H) 2.59 - 2.64 (m, 1 H) 2.72 - 2.84 (m, 3 H) 2.91 (d, J=15.59 Hz, 1 H) 3.22 (s, 3 H) 3.27 (dd, J=9.86, 6.65 Hz, 1 H) 3.29 (s, 3 H) 3.36 - 3.42 (m, 1 H) 3.52 - 3.77 (m, 6 H) 4.22 (s, 1 H) 4.38 (d, J=6.42 Hz, 1 H) 4.56 - 4.66 (m, 2 H) 4.97 (d, J=4.58 Hz, 1 H)
376			897.9	(600 MHz):0.83 (d, J=6.88 Hz, 6 H) 0.91 (t, J=7.34 Hz, 3 H) 1.08 - 1.29 (m, 2 H) 1.11 (d, J=7.34 Hz, 3 H) 1.12 (s, 3 H) 1.15 (d, J=6.42 Hz, 3 H) 1.17 (d, J=7.34 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.33 (s, 3 H) 1.51 - 1.59 (m, 1 H) 1.62 - 1.68 (m, 1 H) 1.71 - 1.88 (m, 3 H) 2.04 (d, J=14.67 Hz, 1 H) 2.10 - 2.21 (m, 1 H) 2.23 - 2.47 (m, 3 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.47 - 2.54 (m, 1 H) 2.61 (d, J=13.30 Hz, 1 H) 2.77 - 2.84 (m, 2 H) 2.84 - 2.96 (m, 5 H) 3.20 - 3.26 (m, 7 H) 3.35 - 3.43 (m, 1 H) 3.52 - 3.60 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 4.23 (s, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.47 (q, J=6.42 Hz, 1 H) 4.62 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H) 7.36 (d, J=8.71 Hz, 2 H) 8.17 (d, J=8.71 Hz, 2 H)
377			817.6	(500 MHz):0.81 (d, J=7.13 Hz, 6 H) 0.85 - 0.91 (m, 9 H) 1.05 - 1.36 (m, 22 H) 1.48 - 1.88 (m, 5 H) 2.00 - 2.07 (m, 1 H) 2.09 - 2.19 (m, 1 H) 2.20 - 2.31 (m, 8 H) 2.35 (s, 3 H) 2.37 - 2.62 (m, 5 H) 2.73 - 2.81 (m, 2 H) 2.86 - 2.94 (m, 1 H) 3.18 - 3.24 (m, 4 H) 3.27 (s, 3 H) 3.34 - 3.45 (m, 2 H) 3.51 - 3.60 (m, 1 H) 3.70 (d, J=8.23 Hz, 1 H) 4.15 - 4.21 (m, 1 H) 4.33 - 4.43 (m, 2 H) 4.57 - 4.66 (m, 1 H) 4.96 (d, J=4.39 Hz, 1 H)
378			859.8	(500 MHz):0.81 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.37 - 1.45 (m, 2 H) 1.49 - 1.58 (m, 4 H) 1.60 - 1.91 (m, 4 H) 2.04 (d, J=14.81 Hz, 1 H) 2.09 - 2.20 (m, 1 H) 2.21 - 2.52 (m, 21 H) 2.65 - 2.82 (m, 4 H) 2.85 - 2.93 (m, 1 H) 3.17 - 3.25 (m, 4 H) 3.27 (s, 3 H) 3.34 - 3.56 (m, 2 H) 3.70 (d, J=8.23 Hz, 1 H) 4.13 - 4.22 (m, 1 H) 4.33 - 4.39 (m, 2 H) 4.58 - 4.66 (m, 1 H) 4.96 (d, J=4.66 Hz, 1 H)

[0854] 

[Table 11-32]

379			861.8	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 1.06 - 1.33 (m, 20 H) 1.48 - 1.89 (m, 5 H) 2.04 (d, J=14.53 Hz, 1 H) 2.09 - 2.52 (m, 20 H) 2.64 - 2.93 (m, 5 H) 3.18 - 3.24 (m, 4 H) 3.28 (s, 3 H) 3.35 - 3.45 (m, 2 H) 3.48 - 3.56 (m, 1 H) 3.65 - 3.72 (m, 5 H) 4.16 - 4.23 (m, 1 H) 4.34 - 4.41 (m, 2 H) 4.58 - 4.66 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H)
380			860.8	(500 MHz): 0.81 (d, J=6.86 Hz, 6 H) 0.85 - 0.92 (m, 3 H) 1.05 - 1.33 (m, 20 H) 1.47 - 1.91 (m, 5 H) 1.98 - 2.20 (m, 3 H) 2.20 - 2.53 (m, 17 H) 2.58 - 2.73 (m, 2 H) 2.73 - 2.92 (m, 7 H) 3.18 - 3.24 (m, 4 H) 3.28 (s, 3 H) 3.33 - 3.46 (m, 2 H) 3.47 - 3.56 (m, 1 H) 3.66 - 3.72 (m, 1 H) 4.13 - 4.22 (m, 2 H) 4.33 - 4.39 (m, 2 H) 4.57 - 4.67 (m, 1 H) 4.94 - 4.98 (m, 1 H)
381			847.9	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.99 (t, J=7.11 Hz, 6 H) 1.06 - 1.28 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 (s, 3 H) 1.14 (d, J=6.42 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.57 - 1.91 (m, 4 H) 2.04 (d, J=14.67 Hz, 1 H) 2.11 - 2.19 (m, 1 H) 2.22 - 2.32 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.39 - 2.68 (m, 11 H) 2.74 - 2.84 (m, 2 H) 2.86 - 2.93 (m, 1 H) 3.19 - 3.22 (m, 1 H) 3.22 - 3.23 (m, 3 H) 3.28 (s, 3 H) 3.35 - 3.44 (m, 1 H) 3.46 - 3.55 (m, 1 H) 3.71 (d, J=7.79 Hz, 1 H) 4.18 (s, 1 H) 4.30 - 4.42 (m, 2 H) 4.62 (s, 1 H) 4.97 (d, J=4.59 Hz, 1 H)
382			845.8	(600 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.12 (s, 3 H) 1.14 (d, J=6.42 Hz, 3 H) 1.15 (d, J=7.79 Hz, 3 H) 1.20 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.66 (m, 2 H) 1.71 - 1.90 (m, 7 H) 2.04 (d, J=15.13 Hz, 1 H) 2.09 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.45 (m, 1 H) 2.45 - 2.59 (m, 9 H) 2.71 (t, J=6.42 Hz, 1 H) 2.74 - 2.94 (m, 3 H) 3.17 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.48 - 3.57 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.17 (s, 1 H) 4.33 - 4.39 (m, 2 H) 4.61 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H)
383			816.8	(600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.03 - 1.28 (m, 4 H) 1.07 - 1.11 (m, 6 H) 1.13 (d, J=6.42 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.22 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.70 (d, 9 H) 1.97 (d, J=14.67 Hz, 1 H) 2.06 (d, J=15.13 Hz, 1 H) 2.11 - 2.21 (m, 1 H) 2.22 - 2.33 (m, 4 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.39 - 2.46 (m, 1 H) 2.46 - 2.53 (m, 1 H) 2.53 - 2.63 (m, 2 H) 2.72 (d, J=15.13 Hz, 1 H) 2.75 - 2.82 (m, 1 H) 2.86 - 2.93 (m, 1 H) 3.22 (dd, J=10.32, 7.11 Hz, 1 H) 3.24 (s, 3 H) 3.29 (s, 3 H) 3.37 - 3.47 (m, 2 H) 3.71 (d, J=7.79 Hz, 1 H) 4.13 - 4.22 (m, 2 H) 4.38 (d, J=7.34 Hz, 1 H) 4.59 - 4.68 (m, 1 H) 4.98 (d, J=5.04 Hz, 1 H)
384			818.8	(600 MHz):0.83 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 - 1.29 (m, 2 H) 1.08 - 1.12 (m, 6 H) 1.15 (d, J=6.42 Hz, 3 H) 1.17 (d, J=7.79 Hz, 3 H) 1.23 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.51 - 1.59 (m, 1 H) 1.62 - 1.93 (m, 4 H) 2.05 (d, J=14.67 Hz, 1 H) 2.08 (d, J=15.13 Hz, 1 H) 2.12 - 2.22 (m, 1 H) 2.23 - 2.34 (m, 2 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.40 - 2.46 (m, 1 H) 2.46 - 2.53 (m, 1 H) 2.55 - 2.71 (m, 4 H) 2.76 - 2.84 (m, 2 H) 2.86 - 2.95 (m, 1 H) 3.23 (dd, J=10.55, 7.34 Hz, 1 H) 3.25 (s, 3 H) 3.30 (s, 3 H) 3.37 - 3.47 (m, 2 H) 3.66 - 3.77 (m, 5 H) 4.16 - 4.26 (m, 2 H) 4.38 (d, J=7.34 Hz, 1 H) 4.64 (s, 1 H) 4.99 (d, J=4.58 Hz, 1 H)

[0855] 

[Table 11-33]

385			898.9	(500 MHz):0.78 - 0.83 (m, 6 H) 0.89 (t, J=7.26 Hz, 3 H) 1.06 - 1.36 (m, 20 H) 1.48 - 1.86 (m, 4 H) 2.01 - 2.44 (m, J=15.29 Hz, 14 H) 2.55 - 2.94 (m, 6 H) 3.17 - 3.28 (m, 7 H) 3.33 - 3.69 (m, 6 H) 4.19 - 4.25 (m, 1 H) 4.36 (d, J=6.88 Hz, 1 H) 4.56 - 4.65 (m, 2 H) 4.72 (d, J=6.12 Hz, 1 H) 4.95 (d, J=4.59 Hz, 1 H) 7.24 - 7.37 (m, 5 H)
386			805.8	(500 MHz):0.81 (d, J=6.86 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 - 1.34 (m, 20 H) 1.48 - 1.89 (m, 5 H) 2.04 (d, J=13.99 Hz, 1 H) 2.11 - 2.53 (m, 18 H) 2.62 - 2.93 (m, 6 H) 3.17 - 3.25 (m, 4 H) 3.27 (s, 3 H) 3.33 - 3.55 (m, 3 H) 3.70 (d, J=7.95 Hz, 1 H) 4.16 - 4.23 (m, 1 H) 4.33 - 4.40 (m, 2 H) 4.57 - 4.68 (m, 1 H) 4.94 - 4.98 (m, 1 H)
387			805.8	(500 MHz):0.81 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.05 - 1.28 (m, 17 H) 1.31 (s, 3 H) 1.48 - 1.92 (m, 5 H) 2.01 - 2.19 (m, 3 H) 2.22 - 2.38 (m, 15 H) 2.38 - 2.54 (m, 3 H) 2.59 - 2.67 (m, 1 H) 2.74 - 2.92 (m, 4 H) 3.18 - 3.30 (m, 7 H) 3.36 - 3.47 (m, 2 H) 3.70 (d, J=8.23 Hz, 1 H) 4.14 - 4.25 (m, 2 H) 4.37 (d, J=7.13 Hz, 1 H) 4.58 - 4.66 (m, 1 H) 4.97 (d, J=4.66 Hz, 1 H)
388			831.8	(500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 1.03 - 1.34 (m, 20 H) 1.48 - 1.92 (m, 6 H) 1.99 - 2.19 (m, 4 H) 2.19 - 2.32 (m, 4 H) 2.27 (s, 3 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.38 - 2.53 (m, 2 H) 2.56 - 2.71 (m, 1 H) 2.74 - 2.83 (m, 2 H) 2.84 - 2.94 (m, 1 H) 3.15 - 3.25 (m, 4 H) 3.28 (s, 3 H) 3.34 - 3.46 (m, 4 H) 3.70 (d, J=8.03 Hz, 1 H) 4.18 (d, 2 H) 4.36 (d, J=7.26 Hz, 1 H) 4.43 - 4.57 (m, 1 H) 4.58 - 4.68 (m, 1 H) 4.97 (d, J=4.59 Hz, 1 H)
389			817.8	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.26 Hz, 3 H) 1.05 - 1.33 (m, 20 H) 1.48 - 1.92 (m, 6 H) 1.98 - 2.20 (m, 3 H) 2.21 - 2.33 (m, 9 H) 2.35 (s, 3 H) 2.38 - 2.67 (m, 3 H) 2.73 - 2.92 (m, 7 H) 3.18 - 3.26 (m, 4 H) 3.28 (s, 3 H) 3.35 - 3.47 (m, 3 H) 3.70 (d, J=8.03 Hz, 1 H) 4.14 - 4.23 (m, 2 H) 4.37 (d, J=7.26 Hz, 1 H) 4.58 - 4.67 (m, 1 H) 4.97 (d, J=4.97 Hz, 1 H)
390			817.7	mixture of diastereomers (500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.26 Hz, 3 H) 1.03 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.46 - 1.91 (m, 7 H) 2.06 (d, J=14.91 Hz, 1 H) 2.10 - 2.31 (m, 11 H) 2.34 (s, 3 H) 2.37 - 2.53 (m, 3 H) 2.61 - 2.81 (m, 2 H) 2.82 - 3.00 (m, 3 H) 3.16 - 3.25 (m, 4 H) 3.27 (s, 3 H) 3.34 - 3.56 (m, 3 H) 3.69 (d, J=8.03 Hz, 1 H) 4.11 - 4.22 (m, 2 H) 4.36 (d, J=7.26 Hz, 1 H) 4.57 - 4.67 (m, 1 H) 4.97 (d, J=4.97 Hz, 1 H)

[0856] 

[Table 11-34]

391			833.8	(500 MHz):0.81 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.06 - 1.32 (m, 20 H) 1.47 - 1.90 (m, 7 H) 2.03 (d, J=15.08 Hz, 1 H) 2.10 - 2.53 (m, 22 H) 2.60 - 2.66 (m, 2 H) 2.74 - 2.93 (m, 3 H) 3.17 - 3.24 (m, 4 H) 3.27 (s, 3 H) 3.33 - 3.56 (m, 3 H) 3.70 (d, J=7.95 Hz, 1 H) 4.14 - 4.21 (m, 1 H) 4.32 - 4.39 (m, 2 H) 4.57 - 4.67 (m, 1 H) 4.96 (d, J=4.66 Hz, 1 H)
392			849.9	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.26 Hz, 3 H) 1.06 - 1.30 (m, 17 H) 1.32 (s, 3 H) 1.47 - 1.86 (m, 5 H) 2.05 (d, J=15.29 Hz, 1 H) 2.10 - 2.56 (m, 23 H) 3.16 - 3.57 (m, 15 H) 3.69 (d, J=8.41 Hz, 1 H) 4.20 - 4.26 (m, 1 H) 4.35 (d, J=7.26 Hz, 1 H) 4.48 - 4.65 (m, 2 H) 4.97 (d, J=4.97 Hz, 1 H)
393			849.8	(500 MHz):0.81 (d, J=6.86 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 - 1.28 (m, 17 H) 1.31 (s, 3 H) 1.49 - 1.89 (m, 5 H) 2.00 - 2.55 (m, 19 H) 2.57 - 2.94 (m, 5 H) 3.17 - 3.29 (m, 7 H) 3.35 - 3.72 (m, 9 H) 4.17 - 4.24 (m, 1 H) 4.32 - 4.43 (m, 2 H) 4.58 - 4.66 (m, 1 H) 4.95 (d, J=5.49 Hz, 1 H)
394			831.8	mixture of diastereomers (500 MHz):0.81 (d, J=6.58 Hz, 6 H) 0.88 (t, J=7.27 Hz, 3 H) 1.04 - 1.33 (m, 20 H) 1.47 - 1.92 (m, 7 H) 2.00 - 3.00 (m, 25 H) 3.17 - 3.30 (m, 7 H) 3.35 - 3.46 (m, 2 H) 3.65 - 3.72 (m, 3 H) 4.11 - 4.23 (m, 2 H) 4.33 - 4.42 (m, 1 H) 4.57 - 4.67 (m, 1 H) 4.93 - 4.99 (m, 1 H)
395			806.7	mixture of diastereomers (600 MHz):0.76 - 0.83 (m, 6 H) 0.86 - 0.92 (m, 3 H) 0.97 (d, J=6.42 Hz, 3 H) 1.05 - 1.28 (m, 14 H) 1.07 (d, J=7.34 Hz, 3 H) 1.36 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.61 - 1.69 (m, 1 H) 1.70 - 1.85 (m, 3 H) 2.03 - 2.09 (m, 1 H) 2.09 - 2.17 (m, 1 H) 2.24 - 2.44 (m 3 H) 2.28 (s, 6 H) 2.35 - 2.37 (m, 3 H) 2.48 - 2.57 (m, 1 H) 2.67 - 2.95 (m, 5 H) 3.21 (s, 3 H) 3.23 - 3.27 (m, 1 H) 3.29 (s, 3 H) 3.34 - 3.43 (m, 2 H) 3.49 - 3.58 (m, 2 H) 3.64 (d, J=7.79 Hz, 1 H) 4.16 (s, 1 H) 4.34 (d, J=7.34 Hz, 1 H) 4.50 - 4.55 (m, 1 H) 4.56 - 4.65 (m, 1 H) 4.94 (d, J=4.58 Hz, 1 H), and (600 MHz):0.76 - 0.83 (m, 6 H) 0.86 - 0.92 (m, 3 H) 1.05 (d, J=6.42 Hz, 3 H) 1.05 - 1.28 (m 14 H) 1.10 (d, J=7.34 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.58 (m, 1 H) 1.61 - 1.69 (m, 1 H) 1.70 - 1.85 (m, 3 H) 2.03 - 2.09 (m, 1 H) 2.09 - 2.17 (m, 1 H) 2.24 - 2.44 (m 3 H) 2.27 (s, 6 H) 2.35 - 2.37 (m, 3 H) 2.48 - 2.57 (m, 2 H) 2.61 - 2.66 (m, 1 H) 2.67 - 2.95 (m, 3 H) 3.21 (s, 3 H) 3.27 - 3.42 (m, 3 H) 3.29 (s, 3 H) 3.49 - 3.58 (m, 1 H) 3.60 - 3.65 (m, 1 H) 3.68 (d, J=8.71 Hz, 1 H) 4.24 (s, 1 H) 4.43 (d, J=5.50 Hz, 1 H) 4.56 - 4.65 (m, 2 H) 4.97 (d, J=5.04 Hz, 1 H)

[0857] 

[Table 11-35]

396			818.8	(600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.84 - 0.91 (m, 9 H) 1.06 - 1.28 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 (s, 3 H) 1.14 (d, J=4.13 Hz, 3 H) 1.15 (d, J=5.04 Hz, 3 H) 1.19 (d, J=5.96 Hz, 3 H) 1.29 - 1.48 (m, 4 H) 1.31 (s, 3 H) 1.48 - 1.57 (m, 1 H) 1.59 - 1.65 (m, 1 H) 1.68 - 1.79 (m, 1 H) 1.79 - 1.89 (m, 2 H) 2.04 (d, J=14.67 Hz, 1 H) 2.10 - 2.19 (m, 1 H) 2.21 - 2.31 (m, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.54 (m, 3 H) 2.74 - 2.81 (m, 2 H) 2.90 (d, J=14.67 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.53 - 3.59 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 4.17 (s, 1 H) 4.35 - 4.42 (m, 2 H) 4.61 (s, 1 H) 4.96 (d, J=4.58 Hz, 1 H)
397			833.8	(600 MHz):0.77 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.02 - 1.06 (m, 6 H) 1.06 - 1.27 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 (s, 3 H) 1.13 - 1.16 (m, 6 H) 1.20 (d, J=6.42 Hz, 3 H) 1.30 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.59 - 1.66 (m, 1 H) 1.68 - 1.89 (m, 3 H) 2.04 (d, J=16.05 Hz, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.32 (m, 2 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.52 (m, 3 H) 2.64 - 2.80 (m, 6 H) 2.82 (d, J=13.30 Hz, 1 H) 2.85 - 2.93 (m, 1 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.33 - 3.54 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.20 (s, 1 H) 4.33 - 4.40 (m, 2 H) 4.61 (s, 1 H) 4.96 (d, J=4.59 Hz, 1 H)
398			832.8	mixture of diastereomers (600 MHz): 0.80 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.42 (m, 4 H) 1.13 - 1.17 (m, 9 H) 1.20 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.59 - 1.87 (m, 6 H) 2.05 (d, J=14.67 Hz, 1 H) 2.09 - 2.19 (m, 1 H) 2.20 - 2.32 (m, 2 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.37 - 2.60 (m, 4 H) 2.73 - 2.84 (m, 2 H) 2.86 - 2.93 (m, 1 H) 3.18 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.31 - 3.43 (m, 3 H) 3.55 - 3.62 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 3.90 - 3.98 (m, 2 H) 4.19 (s, 1 H) 4.35 (d, J=7.34 Hz, 1 H) 4.45 (q, J=6.27 Hz, 1 H) 4.61 (s, 1 H) 4.96 (d, J=4.58 Hz, 1 H)
399				(600 MHz): 0.89 (d, J=6.42 Hz, 6 H) 0.97 (t, J=7.34 Hz, 3 H) 1.12 - 1.35 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.17 (s, 3 H) 1.20 - 1.25 (m, 6 H) 1.30 (d, J=5.96 Hz, 3 H) 1.39 (s, 3 H) 1.55 - 1.87 (m, 5 H) 1.91 (s, 1 H) 1.96 (dd, J=15.13, 5.04 Hz, 1 H) 2.15 (d, J=14.67 Hz, 1 H) 2.20 - 2.60 (m, 9 H) 2.37 (s, 6 H) 2.43 (s, 3 H) 2.71 - 3.10 (m, 6 H) 3.29 (dd, J=10.55, 7.34 Hz, 1 H) 3.32 (s, 3 H) 3.36 (s, 3 H) 3.44 - 3.53 (m, 2 H) 3.57 - 3.63 (m, 1 H) 3.78 (d, J=8.25 Hz, 1 H) 4.23 (s, 1 H) 4.28 (q, J=6.42 Hz, 1 H) 4.45 (d, J=7.34 Hz, 1 H) 4.70 (s, 1 H) 5.06 (d, J=5.04 Hz, 1 H)
400			907.7	mixture of diastereomers (600 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.04 - 1.32 (m, 22 H) 1.46 - 1.87 (m, 5 H) 1.98 - 2.93 (m, 23 H) 3.15 - 3.29 (m, 7 H) 3.32 - 3.60 (m, 4 H) 3.65 - 3.74 (m, 2 H) 4.14 - 4.21 (m, 1 H) 4.31 - 4.40 (m, 2 H) 4.55 - 4.66 (m, 1 H) 4.95 (d, J=5.04 Hz, 1 H) 7.20 - 7.32 (m, 5 H)
401			874.7	(600 MHz):0.77 - 0.91 (m, 9 H) 1.06 - 1.34 (m, 20 H) 1.48 - 1.90 (m, 5 H) 2.00 - 2.59 (m, 28 H) 2.66 - 2.93 (m, 5 H) 3.16 - 3.26 (m, 5 H) 3.28 (s, 3 H) 3.34 - 3.56 (m, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.15 - 4.23 (m, 1 H) 4.34 - 4.39 (m, 2 H) 4.58 - 4.66 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H)

[0858] 

[Table 11-36]

402			817.6	mixture of diastereomers (600 MHz):0.76 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.40 - 2.07 (m, 7 H) 2.09 - 2.58 (m, 14 H) 2.62 - 3.04 (m, 8 H) 3.14 - 3.24 (m, 5 H) 3.27 (s, 3 H) 3.34 - 3.58 (m, 3 H) 3.67 - 3.72 (m, 1 H) 4.16 - 4.24 (m, 1 H) 4.33 - 4.47 (m, 2 H) 4.56 - 4.65 (m, 1 H) 4.94 - 4.98 (m, 1 H)
403			994.7	(600 MHz):0.77 - 0.84 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.47 - 1.89 (m, 5 H) 2.03 (d, J=14.67 Hz, 1 H) 2.10 - 2.51 (m, 20 H) 2.63 - 2.93 (m, 5 H) 3.17 - 3.29 (m, 8 H) 3.35 - 3.55 (m, 6 H) 3.69 (d, J=8.25 Hz, 1 H) 4.14 - 4.23 (m, 1 H) 4.33 - 4.40 (m, 2 H) 4.56 - 4.65 (m, 1 H) 4.96 (d, J=5.04 Hz, 1 H) 5.11 (s, 2 H) 7.27 - 7.37 (m, 5H)
404			860.6	(600 MHz):0.76 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.06 - 1.33 (m, 20 H) 1.48 - 1.90 (m, 5 H) 2.04 (d, J=15.13 Hz, 1 H) 2.11 - 2.53 (m, 22 H) 2.66 - 2.93 (m, 8 H) 3.18 - 3.25 (m, 4 H) 3.28 (s, 3 H) 3.35 - 3.56 (m, 2 H) 3.70 (d, J=7.79 Hz, 1 H) 4.15 - 4.22 (m, 1 H) 4.34 - 4.40 (m, 2 H) 4.58 - 4.66 (m, 1 H) 4.96 (d, J=4.59 Hz, 1 H)
405			748.4	(600 MHz):0.78 - 0.82 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.16 (s, 3 H) 1.16 - 1.17 (m, 1 H) 1.17 - 1.19 (m, 1 H) 1.20 (d, J=5.96 Hz, 3 H) 1.24 (d, J=6.88 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.57 (m, 1 H) 1.62 - 1.85 (m, 3 H) 1.88 (dd, J=15.36, 5.27 Hz, 1 H) 2.10 - 2.27 (m, 2 H) 2.24 (d, J=15.13 Hz, 1 H) 2.29 (s, 6 H) 2.30 - 2.32 (m, 1 H) 2.36 (s, 3 H) 2.38 - 2.44 (m, 1 H) 2.49 - 2.55 (m, 1 H) 2.77 - 2.99 (m, 4 H) 3.17 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.48 - 3.57 (m, 1 H) 3.67 (d, J=7.79 Hz, 1 H) 4.06 - 4.14 (m, 1 H) 4.40 (d, J=6.88 Hz, 1 H) 4.48 (q, J=6.88 Hz, 1 H) 4.58 - 4.68 (m, 1 H) 4.88 (d, J=4.59 Hz, 1 H)
406				(600 MHz): 0.79 (d, J=6.42 Hz, 6 H) 0.87 (t, J=7.34 Hz, 3 H) 1.04 - 1.25 (m, 2 H) 1.07 (d, J=7.34 Hz, 3 H) 1.08 (s, 3 H) 1.12 (d, J=6.42 Hz, 3 H) 1.14 (d, J=7.79 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.29 (s, 3 H) 1.44 - 1.91 (m, 7 H) 2.05 (d, J=15.13 Hz, 1 H) 2.10 - 2.53 (m, 9 H) 2.27 (s, 6 H) 2.33 (s, 3 H) 2.63 - 2.98 (m, 6 H) 3.16 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.27 (s, 3 H) 3.35 - 3.43 (m, 2 H) 3.47 - 3.53 (m, 1 H) 3.68 (d, J=8.25 Hz, 1 H) 4.14 (s, 1 H) 4.18 (q, J=6.11 Hz, 1 H) 4.35 (d, J=7.34 Hz, 1 H) 4.61 (s, 1 H) 4.96 (d, J=5.04 Hz, 1 H)
407			763.2	(600 MHz):0.77 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.14 (d, J=7.34 Hz, 3 H) 1.15 - 1.17 (m, 1 H) 1.17 (s, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.21 - 1.25 (m, 1 H) 1.26 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.48 - 1.57 (m, 1 H) 1.62 - 1.83 (m, 3 H) 1.83 (dd, J=15.13, 5.04 Hz, 1 H) 2.05 - 2.24 (m, 2 H) 2.22 (d, J=15.13 Hz, 1 H) 2.27 - 2.30 (m, 1 H) 2.32 (s, 6 H) 2.36 (s, 3 H) 2.39 - 2.46 (m, 1 H) 2.50 - 2.58 (m, 1 H) 2.77 - 2.85 (m, 1 H) 2.89 - 2.96 (m, 1 H) 3.07 (s, 1 H) 3.20 (s, 3 H) 3.20 - 3.24 (m, 1 H) 3.34 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.46 - 3.55 (m, 2 H) 3.52 (d, J=4.58 Hz, 1 H) 3.66 (d, J=7.79 Hz, 1 H) 4.05 - 4.11 (m, 1 H) 4.37 - 4.46 (m, 2 H) 4.56 - 4.66 (m, 1 H) 4.90 (d, J=5.04 Hz, 1 H)
408			779.4	(600 MHz):0.72 - 0.78 (m, 6 H) 0.84 (t, J=7.34 Hz, 3 H) 1.02 (d, J=7.34 Hz, 3 H) 1.04 - 1.08 (m, 1 H) 1.10 (d, J=7.34 Hz, 3 H) 1.14 - 1.18 (m, 6 H) 1.17 - 1.20 (m, 1 H) 1.22 (d, J=6.42 Hz, 3 H) 1.26 (s, 3 H) 1.45 - 1.54 (m, 1 H) 1.56 - 1.77 (m, 3 H) 1.80 (dd, J=15.13, 5.04 Hz, 1 H) 2.06 - 2.10 (m, 6 H) 2.13 - 2.43 (m, 7 H) 2.67 (d, J=13.76 Hz, 1 H) 2.71 - 2.81 (m, 2 H) 2.83 - 2.90 (m, 1 H) 3.13 - 3.16 (m, 9 H) 3.17 - 3.23 (m, 1 H) 3.29 (s, 3 H) 3.30 - 3.35 (m, 1 H) 3.44 - 3.52 (m, 1 H) 3.62 - 3.67 (m, 1 H) 4.01 - 4.09 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.39 (q, J=6.57 Hz, 1 H) 4.53 - 4.61 (m, 1 H) 4.83 (d, J=4.13 Hz, 1 H)

[0859] 

[Table 11-37]

409			762.5	(600 MHz):0.78 - 0.82 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.11 (m, 1 H) 1.14 (d, J=7.34 Hz, 3 H) 1.17 (s, 3 H) 1.17 - 1.19 (m, 1 H) 1.20 (d, J=5.96 Hz, 3 H) 1.23 (d, J=6.88 Hz, 3 H) 1.32 (s, 3H) 1.50 - 1.57 (m, 1 H) 1.61 - 1.87 (m, 3 H) 2.13 (m, 1 H) 2.20 (d, J=15.13 Hz, 1 H) 2.23 - 2.26 (m, 2 H) 2.26 - 2.32 (m, 7 H) 2.36 (s, 3 H) 2.38 (s, 3 H) 2.39 - 2.45 (m, 1 H) 2.45 - 2.54 (m, 1 H) 2.69 - 2.73 (m, 2 H) 2.77 - 2.83 (m, 1 H) 2.87 - 2.94 (m, 1 H) 3.17 - 3.20 (m, 1 H) 3.20 (s, 3 H) 3.34 (s, 3 H) 3.38 - 3.45 (m, 1 H) 3.46 - 3.53 (m, 1 H) 3.66 (d, J=7.34 Hz, 1 H) 4.05 - 4.12 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.43 (q, J=6.42 Hz, 1 H) 4.58 - 4.66 (m, 1 H) 4.87 (d, J=4.58 Hz, 1 H)
410			776.5	(600 MHz):0.77 - 0.83 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.12 - 1.17 (m, 8 H) 1.16 (s, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.46 (dd, J=15.36, 5.27 Hz, 1 H) 1.49 - 1.57 (m, 1 H) 1.63 - 1.87 (m, 3 H) 2.15 - 2.24 (m, 4 H) 2.25 - 2.33 (m, 7 H) 2.34 - 2.37 (m, 9 H) 2.39 - 2.45 (m, 1 H) 2.55 - 2.64 (m, 1 H) 2.74 (d, J=14.67 Hz, 1 H) 2.77 - 2.83 (m, 1 H) 2.87 - 2.92 (m, 1 H) 3.16 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.59 - 3.66 (m, 1 H) 3.68 (d, J=7.79 Hz, 1 H) 4.04 - 4.09 (m, 1 H) 4.45 (d, J=7.34 Hz, 1 H) 4.59 (q, J=6.72 Hz, 1 H) 4.61 - 4.66 (m, 1 H) 4.82 (d, J=5.04 Hz, 1 H)
411			790.4	(600 MHz):0.77 - 0.93 (m, 9 H) 1.08 - 1.16 (m, 6 H) 1.15 - 1.18 (m, 1 H) 1.19 (d, J=6.42 Hz, 3 H) 1.21 - 1.25 (m, 7 H) 1.31 (s, 3 H) 1.33 - 1.43 (m, 1 H) 1.51 - 1.58 (m, 1 H) 1.69 - 1.88 (m, 3 H) 2.13 - 2.49 (m, 14 H) 2.54 - 2.63 (m, 1 H) 2.80 - 2.92 (m, 2 H) 3.15 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.37 (s, 3 H) 3.39 - 3.48 (m, 2 H) 3.60 - 3.66 (m, 2 H) 3.83 (d, J=10.55 Hz, 1 H) 4.13 - 4.19 (m, 1 H) 4.45 (d, J=6.88 Hz, 1 H) 4.63 - 4.71 (m, 1 H) 4.90 (d, J=5.04 Hz, 1 H) 4.91 - 4.95 (m, 1 H)
412			791.7	(500 MHz): 0.80 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.06 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.88 (m, 4 H) 2.26 (s, 6 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.37 - 2.57 (m, 3 H) 2.65 - 2.84 (m, 5 H) 2.86 - 2.93 (m, 1 H) 3.14 - 3.23 (m, 1 H) 3.20 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.54 (m, 2 H) 3.66 (d, J=7.95 Hz, 1 H) 4.05 - 4.14 (m, 1 H) 4.33 - 4.48 (m, 2 H) 4.58 - 4.67 (m, 1 H) 4.85 - 4.89 (m, 1 H)
413			805.7	(500 MHz): 0.80 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.05 - 1.24 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.88 (m, 6 H) 2.08 - 2.33 (m, 5 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.59 (m, 3 H) 2.63 - 2.84 (m, 6 H) 2.85 - 2.94 (m, 1 H) 3.09 - 3.24 (m, 1 H) 3.20 (s, 3 H) 3.34 (s, 3 H) 3.36 - 3.55 (m, 2 H) 3.66 (d, J=7.95 Hz, 1 H) 4.04-4.13 (m, 1 H) 4.34 - 4.47 (m, 2 H) 4.54 - 4.68 (m, 1 H) 4.86 (d, J=4.66 Hz, 1 H)
414			819.7	(500 MHz): 0.80 (d, J=6.58 Hz, 6 H) 0.88 (t, J=7.27 Hz, 3 H) 1.04 - 1.25 (m, 17 H) 1.31 (s, 3 H) 1.39 - 1.88 (m, 8 H) 2.08 - 2.33 (m, 6 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.64 (m, 4 H) 2.65 - 2.94 (m, 5 H) 3.15 - 3.23 (m, 1 H) 3.20 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.68 (m, 3 H) 3.99 - 4.14 (m, 1 H) 4.33 - 4.50 (m, 2 H) 4.58 - 4.68 (m, 1 H) 4.83 - 4.89 (m, 1 H)

[0860] 

[Table 11-38]

415			792.7	(500 MHz):0.80 (d, J=6.86 Hz, 9 H) 0.89 (t, J=7.40 Hz, 3 H) 1.05 - 1.12 (m, 4 H) 1.12 - 1.22 (m, 10H) 1.23 - 1.28 (m, 3 H) 1.31 (s, 3 H) 1.48 - 1.66 (m, 2 H) 1.68 - 1.88 (m, 2 H) 2.26 (s, 5 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.50 (m, 2 H) 2.59 - 2.67 (m, 1 H) 2.74 - 2.93 (m, 5 H) 3.14 - 3.26 (m, 2 H) 3.34 (s, 3 H) 3.36 - 3.68 (m, 4 H) 4.06 - 4.16 (m, 1 H) 4.37 (d, J=7.13 Hz, 1 H) 4.44 (d, 1 H) 4.58-4.67 (m, 1 H) 4.89 (d, J=4.66 Hz, 1 H)
416			816.7	(500 MHz): 0.81 (d, J=7.13 Hz, 6 H) 0.88 (t, J=7.27 Hz, 3 H) 1.07 - 1.16 (m, 13 H) 1.16 - 1.22 (m, 4 H) 1.32 (s, 3 H) 1.36 - 1.89 (m, 12 H) 2.10 - 2.33 (m, 6 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.39 - 2.48 (m, 1 H) 2.50 - 2.66 (m, 2 H) 2.70 (d, J=14.54 Hz, 1 H) 2.85 (d, 2 H) 3.14 - 3.30 (m, 2 H) 3.22 (s, 3 H) 3.36 (s, 3 H) 3.38 - 3.47 (m, 1 H) 3.60 - 3.72 (m, 2 H) 4.02 - 4.10 (m, 1 H) 4.47 (d, J=7.13 Hz, 1 H) 4.59- 4.67 (m, 2 H) 4.82 (d, J=5.21 Hz, 1 H)
417			806.7	(500 MHz):0.80 (d, J=6.87 Hz, 6 H) 0.89 (t, J=7.44 Hz, 3 H) 1.04 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.48 - 1.85 (m, 6 H) 1.90 - 1.97 (m, 1 H) 2.18 - 2.34 (m, 4 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.37 - 2.49 (m, 2 H) 2.64 - 2.96 (m, 6 H) 3.12 - 3.26 (m, 2 H) 3.19 (s, 2 H) 3.33 (s, 3 H) 3.35 - 3.51 (m, 2 H) 3.65 (d, J=8.01 Hz, 1 H) 3.75 - 3.79 (m, 2 H) 4.07 - 4.16 (m, 1 H) 4.33 - 4.47 (m, 2 H) 4.57-4.66 (m, 1 H) 4.88 (d, J=4.58 Hz, 1 H)
418			817.8	(500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.26 Hz, 3 H) 1.03- 1.22 (m, 17 H) 1.31 (s, 3 H) 1.46 - 1.88 (m, 6 H) 2.25 (s, 4 H) 2.25 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.46 (m, 1 H) 2.48 - 2.74 (m, 5 H) 2.76 - 2.93 (m, 6 H) 3.12 - 3.24 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.56 - 3.65 (m, 1 H) 3.68 (d, J=7.65 Hz, 1 H) 4.01 - 4.11 (m, 1 H) 4.28 - 4.37 (m, 1 H) 4.45 (d, J=7.65 Hz, 1 H) 4.54 - 4.68 (m, 2 H) 4.83 (d, J=5.35 Hz, 1 H)
419			819.7	(500 MHz):0.80 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.27 Hz, 3 H) 1.03 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.94 (m, 5 H) 1.97 - 2.07 (m, 1 H) 2.09 - 2.45 (m, 6 H) 2.20 (s, 6 H) 2.26 (s, 7 H) 2.35 (s, 3 H) 2.45 - 2.53 (m, 1 H) 2.58 - 2.74 (m, 3 H) 2.75 - 2.84 (m, 2 H) 2.85 - 2.94 (m, 1 H) 3.13 - 3.29 (m, 1 H) 3.21 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.56 (m, 2 H) 3.67 (d, J=7.95 Hz, 1 H) 4.04 - 4.14 (m, 1 H) 4.36 - 4.51 (m, 2 H) 4.57 - 4.69 (m, 1 H) 4.86 (d, J=4.94 Hz, 1 H)
420			820.7	(500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.26 Hz, 3 H) 1.04 - 1.28 (m, 17 H) 1.32 (s, 3 H) 1.47 - 1.88 (m, 8 H) 1.98 - 2.19 (m, 2 H) 2.17 - 2.55 (m, 6 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.67 - 2.96 (m, 5 H) 3.14 - 3.26 (m, 1 H) 3.20 (s, 3 H) 3.34 (s, 3 H) 3.32 - 3.53 (m, 2 H) 3.53 - 3.69 (m, 3 H) 4.04 - 4.16 (m, 1 H) 4.32 - 4.48 (m, 2 H) 4.56-4.68 (m, 1 H) 4.89 (d, J=5.35 Hz, 1 H)
421			818.7	(500 MHz): 0.80 (d, J=7.13 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.06 - 1.22 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.90 (m, 5 H) 2.10 - 2.37 (m, 5 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.37 - 2.46 (m, 1 H) 2.47 - 2.61 (m, 3 H) 2.62 - 2.93 (m, 5 H) 3.15 - 3.25 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.54 - 3.63 (m, 1 H) 3.64 - 3.70 (m, 5 H) 4.02-4.13 (m, 1 H) 4.43 (d, J=7.13 Hz, 1 H) 4.53 - 4.67 (m, 2 H) 4.84 (d, J=4.94 Hz, 1 H)

[0861] 

[Table 11-39]

422			806.7	(500 MHz):0.80 (d, J=7.13 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.05 - 1.24 (m, 17 H) 1.31 (s, 3 H) 1.47 - 1.87 (m, 4 H) 1.99 - 2.54 (m, 7 H) 2.25 (s, 6 H) 2.35 (s, 3 H) 2.67 - 2.94 (m, 5 H) 3.13 - 3.24 (m, 1 H) 3.20 (s, 3 H) 3.33 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.55 (m, 5 H) 3.67 (d, J=7.68 Hz, 1 H) 4.05-4.13 (m, 1 H) 4.39 (d, J=7.13 Hz, 1 H) 4.46 (q, J=6.58 Hz, 1 H) 4.56-4.69 (m, 1 H) 4.85 (d, J=4.66 Hz, 1 H)
423			806.7	(500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.26 Hz, 3 H) 1.06 - 1.28 (m, 17 H) 1.32 (s, 3 H) 1.49 - 1.87 (m, 5 H) 2.10 - 2.52 (m, 7 H) 2.26 (s, 6 H) 2.34 - 2.36 (m, 3 H) 2.36 (s, 3 H) 2.58 - 2.66 (m, 1 H) 2.69 - 2.93 (m, 4 H) 3.15 - 3.29 (m, 1 H) 3.21 (s, 3 H) 3.34 (s, 3 H) 3.37 - 3.70 (m, 5 H) 4.06-4.11 (m, 1 H) 4.40 (d, J=7.65 Hz, 1 H) 4.50 (q, J=6.88 Hz, 1 H) 4.59-4.67 (m, 1 H) 4.86 (d, J=4.59 Hz, 1 H)
424			804.7	(500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.85 - 0.92 (m, 6 H) 1.05 - 1.25 (m, 17 H) 1.27 - 1.36 (m, 5 H) 1.38 - 1.47 (m, 2 H) 1.48 - 1.88 (m, 4 H) 2.06 - 2.61 (m, 9 H) 2.26 (s, 6 H) 2.35 (s, 3 H) 2.66 - 2.84 (m, 3 H) 2.86 - 2.94 (m, 1 H) 3.15 - 3.25 (m, 1 H) 3.21 (s, 3 H) 3.32 - 3.55 (m, 2 H) 3.34 (s, 3 H) 3.66 (d, J=8.41 Hz, 1 H) 4.04 - 4.14 (m, 1 H) 4.37 - 4.49 (m, 2 H) 4.58 - 4.69 (m, 1 H) 4.86 (d, J=4.59 Hz, 1 H)
425			801.6	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.26 Hz, 3 H) 1.07 - 1.29 (m, 17 H) 1.32 (s, 3 H) 1.49 - 1.88 (m, 5 H) 2.10 - 2.55 (m, 8 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.66 - 3.02 (m, 6 H) 3.15-3.51 (m, 3 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.66 (d, J=7.65 Hz, 1 H) 4.08 - 4.16 (m, 1 H) 4.36 - 4.45 (m, 2 H) 4.58 - 4.68 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H)
426			838.6	(500 MHz):0.80 (d, J=6.86 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 - 1.23 (m, 17 H) 1.32 (s, 3 H) 1.49 - 1.86 (m, 4 H) 2.26 (s, 5 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.51 (m, 2 H) 2.67 - 2.84 (m, 3 H) 2.86 - 2.94 (m, 1 H) 3.15 - 3.22 (m, 1 H) 3.20 (s, 3 H) 3.33 (s, 3 H) 3.38 - 3.52 (m, 2 H) 3.63 - 3.80 (m, 3 H) 4.06 - 4.13 (m, 1 H) 4.34 - 4.45 (m, 2 H) 4.58 - 4.68 (m, 1 H) 4.88 (d, J=4.66 Hz, 1 H) 7.20 - 7.35 (m, 5 H)
427			839.6	(500 MHz): 0.80 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.04 - 1.35 (m, 20 H) 1.46 - 1.95 (m, 4 H) 2.07 - 2.48 (m, 7 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.66 (d, J=12.07 Hz, 1 H) 2.76 - 2.84 (m, 2 H) 2.85 - 2.93 (m, 1 H) 3.14 - 3.49 (m, 4 H) 3.19 (s, 3 H) 3.33 (s, 3 H) 3.61 - 3.69 (m, 2 H) 3.80 (d, J=13.44 Hz, 1 H) 4.06 - 4.15 (m, 1 H) 4.33 - 4.44 (m, 2 H) 4.58 - 4.67 (m, 1 H) 4.88 (d, J=4.94 Hz, 1 H) 7.21 - 7.25 (m, 1 H) 7.59 - 7.64 (m, 1 H) 8.45 - 8.58 (m, 2 H)
428			799.6	(500 MHz):0.76 - 0.84 (m, 6 H) 0.86 - 0.92 (m, 6 H) 1.04 - 1.27 (m, 14 H) 1.30 (s, 3 H) 1.50 - 1.87 (m, 5 H) 2.09 - 2.56 (m, 6 H) 2.32 (s, 6 H) 2.37 (s, 3 H) 2.79 - 2.95 (m, 2 H) 3.16 - 3.25 (m, 1 H) 3.19 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.46 (m, 2 H) 3.63 (d, J=7.64 Hz, 1 H) 4.11 - 4.29 (m, 3 H) 4.35 (d, J=6.88 Hz, 1 H) 4.48 - 4.68 (m, 2 H) 4.98 (d, J=4.59 Hz, 1 H) 7.00 (s, 1 H) 7.07 - 7.10 (m, 1 H) 7.60 (s, 1 H)
429			824.7	(500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.91 (t, J=7.26 Hz, 3 H) 1.06 - 1.36 (m, 20 H) 1.51 - 1.89 (m, 4 H) 2.01 - 2.55 (m, 7 H) 2.31 (s, 6 H) 2.38 (s, 3 H) 2.79 - 2.88 (m, 1 H) 2.89 - 2.97 (m, 1 H) 3.14 - 3.52 (m, 5 H) 3.23 (s, 3 H) 3.37 (s, 3 H) 3.68 (d, J=8.03 Hz, 1 H) 4.17 - 4.25 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.50 (q, J=6.75 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 5.01 (d, J=4.97 Hz, 1 H) 6.62 (d, J=8.03 Hz, 2 H) 6.69 (t, J=7.26 Hz, 1 H) 7.18 (t, J=7.84 Hz, 2 H)
430			774.6	(500 MHz):0.77 - 0.93 (m, 9 H) 1.07 - 1.28 (m, 17 H) 1.32 (s, 3 H) 1.40 - 1.89 (m, 4 H) 2.10 - 2.61 (m, 7 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.75 - 2.92 (m, 2 H) 3.14 - 3.45 (m, 3 H) 3.22 (s, 3 H) 3.38 (s, 3 H) 3.57 - 3.71 (m, 3 H) 4.10 - 4.19 (m, 1 H) 4.43 - 4.49 (m, 1 H) 4.57 - 4.69 (m, 1 H) 4.86 - 4.93 (m, 2 H) 5.00 - 5.04 (m, 1 H)

[0862] 

[Table 11-40]

431			954.0	(600 MHz):0.82 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.94 (t, J=7.11 Hz, 3 H) 1.11 - 1.29 (m, 17 H) 1.27 (d, J=6.88 Hz, 3 H) 1.31 (s, 3 H) 1.48 - 1.75 (m, 3 H) 1.80 - 1.85 (m, 1 H) 1.88 (dd, J=15.13, 5.04 Hz, 1 H) 2.04 (d, J=14.67 Hz, 1 H) 2.11 - 2.19 (m, 1 H) 2.25 - 2.30 (m, 2 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.36 - 2.66 (m, 9 H) 2.74 - 2.81 (m, 2 H) 2.86 - 2.94 (m, 1 H) 3.18 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.27 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.43 - 3.48 (m, 1 H) 3.71 (d, J=8.25 Hz, 1 H) 3.80 (s, 3 H) 4.15 - 4.22 (m, 1 H) 4.26 - 4.32 (m, 1 H) 4.33 - 4.39 (m, 2 H) 4.59 - 4.66 (m, 1 H) 4.97 (d, J=5.04 Hz, 1 H) 6.84 (d, J=8.25 Hz, 1 H) 6.89 - 6.94 (m, 1 H) 7.17 - 7.22 (m, 1 H) 7.29 - 7.33 (m, 1 H)
432			911.9	mixture of diastereomers (600 MHz):0.80 - 0.88 (m, 6 H) 0.89 - 0.95 (m, 3 H) 1.08 - 1.39 (m, 23 H) 1.49 - 1.91 (m, 4 H) 2.09 - 2.73 (m, 12 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.75 - 2.96 (m, 3 H) 3.15 - 3.56 (m, 9 H) 3.63 - 3.77 (m, 2 H) 4.13 - 4.21 (m, 1 H) 4.36 - 4.48 (m, 2 H) 4.66 - 4.75 (m, 1 H) 4.89 - 4.95 (m, 1 H) 6.70 - 6.90 (m, 3 H) 7.15 (t, J=7.79 Hz, 1 H)
433			911.9	(600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.03 - 1.28 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.13 (s, 3 H) 1.17 (d, J=7.79 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.26 (d, J=6.42 Hz, 3 H) 1.29 - 1.34 (m, 6 H) 1.50 - 1.60 (m, 1 H) 1.60 - 1.68 (m, 1 H) 1.70 - 1.90 (m, 2 H) 2.07 - 2.46 (m, 6 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.46 - 2.73 (m, 7 H) 2.79 - 2.86 (m, 1 H) 2.86 - 2.93 (m, 1 H) 3.19 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.33 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.46 - 3.55 (m, 1 H) 3.65 - 3.77 (m, 2 H) 4.16 (s, 1 H) 4.40 (d, J=7.34 Hz, 1 H) 4.44 (q, J=6.88 Hz, 1 H) 4.67 (s, 1 H) 4.89 (d, J=5.04 Hz, 1 H) 6.71 (dd, J=8.02, 2.52 Hz, 1 H) 6.75 (d, J=7.79 Hz, 1 H) 6.84 - 6.88 (m, 1 H) 7.1 (t, J=7.79 Hz, 1 H)
434			944.0	(500 MHz):0.77 - 0.85 (m, 6 H) 0.90 (t, J=7.40 Hz, 3 H) 1.04 - 1.26 (m, 17 H) 1.30 (s, 3 H) 1.50 - 1.87 (m, 4 H) 1.97 - 2.03 (m, 1 H) 2.10 - 2.52 (m, 6 H) 2.25 (s, 6 H) 2.37 (s, 3 H) 2.61 - 2.69 (m, 2 H) 2.77 - 2.96 (m, 3 H) 3.14 - 3.23 (m, 1 H) 3.15 (s, 3 H) 3.29 - 3.46 (m, 3 H) 3.33 (s, 3 H) 3.60 - 3.67 (m, 2 H) 4.09 - 4.17 (m, 1 H) 4.33 (d, J=7.13 Hz, 1 H) 4.41 (q, J=6.40 Hz, 1 H) 4.59 - 4.68 (m, 1 H) 4.81 (d, J=6.31 Hz, 1 H) 4.89 (d, J=4.94 Hz, 1 H) 7.57 (d, J=8.78 Hz, 2 H) 8.1 (d, J=8.78 Hz, 2 H)
435				(500 MHz): 0.80 (d, J=6.86 Hz, 6 H) 0.88 (t, J=7.40 Hz, 3 H) 1.05 - 1.37 (m, 22 H) 1.39 - 1.88 (m, 8 H) 2.07 - 2.32 (m, 11 H) 2.32 - 2.92 (m, 13 H) 3.15 - 3.23 (m, 4 H) 3.31 - 3.43 (m, 5 H) 3.46 - 3.74 (m, 4 H) 4.05 - 4.13 (m, 1 H) 4.37 - 4.48 (m, 2 H) 4.58 - 4.71 (m, 2 H) 4.86 (d, J=4.66 Hz, 1 H) 7.58 (d, J=8.50 Hz, 2 H) 8.17 - 8.21 (m, 2 H)
436			1042.8	(500 MHz):0.73 - 0.83 (m, 6 H) 0.84 - 0.90 (m, 3 H) 1.03 - 1.87 (m, 32 H) 1.91 - 1.96 (m, 4 H) 2.04-2.91 (m, 20 H) 3.11 - 3.30 (m, 4 H) 3.30 - 3.42 (m, 5 H) 3.45 - 3.55 (m, 1 H) 3.63 - 3.72 (m, 2 H) 4.04 - 4.10 (m, 1 H) 4.35 - 4.47 (m, 2 H) 4.55 - 4.71 (m, 2 H) 4.83 - 4.86 (m, 1 H) 5.68 - 5.76 (m, 1 H) 7.56 - 7.60 (m, 2 H) 8.17 (d, J=8.78 Hz, 2 H)
437			987.0	(600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.10 - 1.22 (m, 2 H) 1.17 (d, J=7.79 Hz, 3 H) 1.18 (s, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.28 (d, J=6.88 Hz, 3 H) 1.34 (s, 3 H) 1.51 - 1.87 (m, 5 H) 2.11 - 2.26 (m, 3 H) 2.28 (s, 6 H) 2.30 - 2.35 (m, 1 H) 2.37 (s, 3 H) 2.41 - 2.46 (m, 1 H) 2.46 - 2.51 (m, 1 H) 2.56 - 2.91 (m, 10 H) 3.20 - 3.24 (m, 4 H) 3.36 (s, 3 H) 3.38 - 3.43 (m, 2 H) 3.45 - 3.50 (m, 1 H) 3.64 - 3.68 (m, 2 H) 4.11 - 4.17 (m, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.43 - 4.48 (m, 1 H) 4.59 - 4.64 (m, 1 H) 4.69 (d, J=6.42 Hz, 1 H) 4.94 (d, J=4.58 Hz, 1 H) 7.60 (d, J=8.71 Hz, 2 H) 8.20 (d, J=8.71 Hz, 2 H)

[0863] 

[Table 11-41]

438			1001.1	(600 MHz):0.82 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.17 (d, J=7.79 Hz, 3 H) 1.18 (s, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.33 (s, 3 H) 1.51 - 1.87 (m, 7 H) 2.10 - 2.34 (m, 4 H) 2.28 (s, 6 H) 2.38 (s, 3 H) 2.40 - 2.92 (m, 11 H) 3.20 (s, 3 H) 3.20 - 3.24 (m, 1 H) 3.36 (s, 3 H) 3.36 - 3.40 (m, 2 H) 3.46 - 3.52 (m, 1 H) 3.66 (d, J=7.79 Hz, 1 H) 3.69 (dd, J=11.00, 3.67 Hz, 1 H) 4.11-4.14 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.42-4.47 (m, 1 H) 4.58 - 4.65 (m, 1 H) 4.71 (d, J=6.88 Hz, 1 H) 4.91 (d, J=4.58 Hz, 1 H) 7.61 (d, J=8.71 Hz, 2 H) 8.20 (d, J=8.71 Hz, 2 H)
439			1015.1	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t J=7.34 Hz, 3 H) 1.08 - 1.24 (m, 8 H) 1.10 (d, J=7.34 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.24 (d, J=6.88 Hz, 3 H) 1.33 (s, 3 H) 1.44 - 1.87 (m, 9 H) 2.10 - 2.34 (m, 4 H) 2.27 (s, 6 H) 2.37 (s, 3 H) 2.40 - 2.51 (m, 4 H) 2.58 - 2.67 (m, 3 H) 2.71 - 2.78 (m, 2 H) 2.79 - 2.92 (m, 2 H) 3.19 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.44 (m, 2 H) 3.47 - 3.53 (m, 1 H) 3.67 (d, J=7.34 Hz, 1 H) 3.71 (dd, J=11.00, 3.67 Hz, 1 H) 4.08 - 4.13 (m, 1 H) 4.39 (d, J=7.34 Hz, 1 H) 4.42 - 4.48 (m, 1 H) 4.58 - 4.64 (m, 1 H) 4.70 (d, J=6.88 Hz, 1 H) 4.87 - 4.90 (m, 1 H) 7.60 (d, J=8.25 Hz, 2 H) 8.20 (d, J=8.71 Hz, 2 H)
440			863.9	(600 MHz):0.82 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.02 (t, J=7.11 Hz, 3 H) 1.10 (d, J=7.79 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 (s, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.25 (d, J=6.88 Hz, 3 H) 1.33 (s, 3 H) 1.50 - 1.87 (m, 4 H) 2.11 - 2.34 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.40 - 2.70 (m, 10 H) 2.73 - 2.85 (m, 3 H) 2.89 - 2.95 (m, 1 H) 3.17 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.36 (s, 3 H) 3.39 - 3.57 (m, 4 H) 3.63 - 3.69 (m, 2 H) 4.08 - 4.13 (m, 1 H) 4.40 (d, J=7.34 Hz, 1 H) 4.43 - 4.47 (m, 1 H) 4.60 - 4.68 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H)
441			878.0	(600 MHz): 0.82 (d, J=6.42 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.04 (t, J=7.11 Hz, 3 H) 1.02 - 1.24 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.18 (s, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.25 (d, J=6.88 Hz, 3 H) 1.34 (s, 3 H) 1.50 - 1.87 (m, 6 H) 2.11 - 2.33 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.39 - 2.85 (m, 13 H) 2.89 - 2.94 (m, 1 H) 3.18 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.36 (s, 3 H) 3.41 - 3.45 (m, 1 H) 3.49 - 3.55 (m, 1 H) 3.61 - 3.69 (m, 2 H) 3.75 - 3.78 (m, 2 H) 3.80 - 3.83 (m, 1 H) 4.08 - 4.12 (m, 1 H) 4.41 (d, J=7.34 Hz, 1 H) 4.43 - 4.48 (m, 1 H) 4.61 - 4.67 (m, 1 H) 4.89 (d, J=4.13 Hz, 1 H)
442			833.9	(500 MHz): 0.80 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.05 - 1.27 (m, 17 H) 1.32 (s, 3 H) 1.48 - 1.87 (m, 4 H) 1.96 (s, 3 H) 2.06 - 2.34 (m, 10 H) 2.36 (s, 3 H) 2.38 - 2.50 (m, 2 H) 2.57 - 2.65 (m, 1 H) 2.72 - 2.93 (m, 6 H) 3.16 - 3.50 (m, 11 H) 3.62 - 3.67 (m, 1 H) 4.07 - 4.15 (m, 1 H) 4.34 - 4.47 (m, 2 H) 4.58 - 4.69 (m, 1 H) 4.89 (d, J=4.66 Hz, 1 H) 5.88 - 5.94 (m, 1 H)
443			869.9	(500 MHz): 0.80 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.04 - 1.35 (m, 20 H) 1.47 - 1.87 (m, 4 H) 2.03 - 2.17 (m, 2 H) 2.20 - 2.38 (m, 13 H) 2.38 - 2.50 (m, 2 H) 2.61 - 2.93 (m, 6 H) 2.95 (s, 3 H) 3.11 - 3.28 (m, 5 H) 3.34 (s, 3 H) 3.37 - 3.52 (m, 2 H) 3.64 (d, J=7.95 Hz, 1 H) 4.09 - 4.16 (m, 1 H) 4.34 - 4.46 (m, 2 H) 4.58 - 4.67 (m, 1 H) 4.76 - 4.92 (m, 2 H)
444			833.9	(500 MHz):0.80 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 - 1.25 (m, 17 H) 1.32 (s, 3 H) 1.48 - 1.88 (m, 6 H) 2.06 - 2.33 (m, 18 H) 2.36 (s, 3 H) 2.38 - 2.94 (m, 8 H) 3.14 - 3.26 (m, 5 H) 3.34 (s, 3 H) 3.38 - 3.56 (m, 2 H) 3.67 (d, J=7.68 Hz, 1 H) 4.06 - 4.13 (m, 1 H) 4.36 - 4.49 (m, 2 H) 4.58 - 4.69 (m, 1 H) 4.86 (d, J=4.94 Hz, 1 H)

[0864] 

[Table 11-42]

445			847.9	(500 MHz):0.80 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.05 - 1.25 (m, 17 H) 1.32 (s, 3 H) 1.42 - 1.87 (m, 8 H) 2.08 - 2.33 (m, 18 H) 2.36 (s, 3 H) 2.37 - 2.65 (m, 4 H) 2.68 - 2.94 (m, 4 H) 3.15 - 3.27 (m, 5 H) 3.34 (s, 3 H) 3.36 - 3.55 (m, 2 H) 3.66 (d, J=7.68 Hz, 1 H) 4.05 - 4.12 (m, 1 H) 4.36 - 4.48 (m, 2 H) 4.58 - 4.69 (m, 1 H) 4.86 (d, J=4.66 Hz, 1 H)
446			928.0	mixture of diastereomers (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.14 - 1.26 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 (d, J=4.13 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.26 - 1.29 (m, 3 H) 1.32 (s, 3 H) 1.46 - 1.88 (m, 4 H) 2.03 - 2.18 (m, 2 H) 2.21 - 2.51 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.54 (dd, J=11.92, 8.71 Hz, 1 H) 2.74 - 2.94 (m, 5 H) 3.07 - 3.29 (m, 3 H) 3.20 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.51 (m, 2 H) 3.67 (d, J=7.79 Hz, 1 H) 3.84 (s, 3 H) 3.87 - 3.96 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.41 - 4.47 (m, 1 H) 4.59 - 4.67 (m, 1 H) 4.86 - 4.92 (m, 1 H) 6.59 - 6.64 (m, 1 H) 6.65 - 6.70 (m, 1 H) 6.74 - 6.79 (m, 1 H) 6.82 - 6.88 (m, 1 H), and (600 MHz):0.81 (d, J=6.42 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.10 (d, J=7.34 Hz, 3 H) 1.14 - 1.26 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 (d, J=4.13 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.26 - 1.29 (m, 3 H) 1.32 (s, 3 H) 1.46 - 1.88 (m, 4 H) 2.03 - 2.18 (m, 2 H) 2.21 - 2.51 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.63 (dd, J=12.38, 3.67 Hz, 1 H) 2.74 - 2.94 (m, 5 H) 3.07 - 3.29 (m, 3 H) 3.20 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.51 (m, 2 H) 3.67 (d, J=7.79 Hz, 1 H) 3.84 (s, 3 H) 3.87 - 3.96 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.41 - 4.47 (m, 1 H) 4.59 - 4.67 (m, 1 H) 4.86 - 4.92 (m, 1 H) 6.59 - 6.64 (m, 1 H) 6.65 - 6.70 (m, 1 H) 6.74 - 6.79 (m, 1 H) 6.82 - 6.88 (m, 1 H)
447			984.0	mixture of diastereomers (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.86 - 0.91 (m, 3 H) 0.91 - 0.99 (m, 3 H) 1.05 - 1.36 (m, 23 H) 1.47 - 1.88 (m, 4 H) 1.95 - 2.03 (m, 1 H) 2.10 - 2.33 (m, 4 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.85 (m, 11 H) 2.88 - 2.95 (m, 1 H) 3.16 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.46 (m, 1 H) 3.49 - 3.58 (m, 1 H) 3.64 - 3.78 (m, 2 H) 3.82 (s, 3 H) 4.05 - 4.15 (m, 1 H) 4.36 - 4.45 (m, 2 H) 4.45 - 4.52 (m, 1 H) 4.57 - 4.67 (m, 1 H) 4.82 - 4.89 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.18 - 7.29 (m, 2 H), and (600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.86 - 0.91 (m, 3 H) 0.91 - 0.99 (m, 3 H) 1.05 - 1.36 (m, 23 H) 1.47 - 1.88 (m, 4 H) 1.95 - 2.03 (m, 1 H) 2.10 - 2.33 (m, 4 H) 2.27 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.85 (m, 11 H) 2.88 - 2.95 (m, 1 H) 3.16 - 3.21 (m, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.37 - 3.46 (m, 1 H) 3.49 - 3.58 (m, 1 H) 3.64 - 3.78 (m, 2 H) 3.83 (s, 3 H) 4.05 - 4.15 (m, 1 H) 4.36 - 4.45 (m, 2 H) 4.45 - 4.52 (m, 1 H) 4.57 - 4.67 (m, 1 H) 4.82 - 4.89 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.18 - 7.29 (m, 2 H)
448			970.0	(600 MHz):0.78 - 0.84 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 - 1.22 (m, 2 H) 1.07 (s, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.13 (d, J=6.42 Hz, 3 H) 1.15 (d, J=7.34 Hz, 3 H) 1.20 (d, J=5.96 Hz, 3 H) 1.29 - 1.34 (m, 6 H) 1.50 - 1.58 (m, 1 H) 1.60 - 1.66 (m, 1 H) 1.70 - 1.88 (m, 3 H) 2.12 - 2.20 (m, 1 H) 2.21 - 2.39 (m, 4 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.42 (d, J=12.84 Hz, 1 H) 2.46 - 2.64 (m, 6 H) 2.67 (d, J=12.84 Hz, 1 H) 2.70 - 2.76 (m, 1 H) 2.77 - 2.84 (m, 1 H) 2.91 (d, J=14.21 Hz, 1 H) 3.18 (dd, J=10.09, 7.34 Hz, 1 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.37 - 3.57 (m, 3 H) 3.60 - 3.68 (m, 2 H) 3.83 (s, 3 H) 4.07 (s, 1 H) 4.36 - 4.48 (m, 3 H) 4.63 (s, 1 H) 4.83 (d, J=5.04 Hz, 1 H) 6.87 (d, J=7.34 Hz, 1 H) 6.94 (t, J=7.11 Hz, 1 H) 7.20 - 7.29 (m, 2 H)

[0865] 

[Table 11-43]

449			822.7	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.90 (t, J=7.11 Hz, 3 H) 1.09 (d, J=7.34 Hz, 3 H) 1.10 - 1.28 (m, 2 H) 1.16 (d, J=7.34 Hz, 3 H) 1.19 (s, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.29 (d, J=6.88 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.87 (m, 4 H) 2.05 (dd, J=15.13, 5.04 Hz, 1 H) 2.08 - 2,19 (m, 1 H) 2.19 - 2.52 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.64 - 2.70 (m, 1 H) 2.78 - 2.94 (m, 4 H) 3.17 - 3.23 (m, 1 H) 3.20 (s, 3 H) 3.29 - 3.41 (m, 1 H) 3.35 (s, 3 H) 3.43 - 3.51 (m, 1 H) 3.53 (dd, J=11.00, 5.04 Hz, 1 H) 3.61 (dd, J=11.00, 5.50 Hz, 1 H) 3.65 - 3.69 (m, 2 H) 3.72 (dd, J=11.00, 4.59 Hz, 1 H) 4.14 (s, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.42 - 4.48 (m, 1 H) 4.62 (s, 1 H) 4.90 (d, J=4.59 Hz, 1 H)
450			913.8	mixture of diastereomers (600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.87 - 0.93 (m, 3 H) 1.07 - 1.36 (m, 17 H) 1.10 (d, J=7.34 Hz, 3 H) 1.48 - 1.88 (m, 4 H) 2.00 - 2.19 (m, 2 H) 2.20 - 2.48 (m, 5 H) 2.28 (s, 6 H) 2.35 - 2.38 (m, 3 H) 2.48 - 3.02 (m 6 H) 3.18 - 3.24 (m, 1 H) 3.21 (s, 3 H) 3.34 - 3.48 (m, 2 H) 3.36 (s, 3 H) 3.61 - 3.68 (m, 1 H) 4.15 (s, 1 H) 4.34 - 4.39 (m, 1 H) 4.41 - 4.47 (m, 1 H) 4.60 - 4.69 (m, 1 H) 4.75 - 4.82 (m, 1 H) 4.93 (d, J=5.04 Hz, 1 H) 7.50 - 7.57 (m, 2 H) 8.18 - 8.23 (m, 2 H)
451			978.8	(600 MHz):0.76 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.05 - 1.34 (m, 20 H) 1.42 - 1.86 (m, 4 H) 1.88 - 2.54 (m, 15 H) 2.60 - 3.00 (m, 4 H) 3.01 - 3.07 (m, 4 H) 3.13 - 3.68 (m, 13 H) 4.10 - 4.28 (m, 1 H) 4.32 - 4.47 (m, 2 H) 4.67 (d, J=7.79 Hz, 2 H) 4.87 - 4.92 (m, 1 H) 7.59 (d, J=8.25 Hz, 2 H) 7.92 (d, J=8.25 Hz, 2 H)
452			898.9	(500 MHz):0.76 - 0.85 (m, 6 H) 0.90 (t, J=7.40 Hz, 3 H) 1.05 - 1.26 (m, 17 H) 1.31 (s, 3 H) 1.48 - 1.66 (m, 2 H) 1.69 - 1.87 (m, 2 H) 2.04 (dd, J=15.08, 5.21 Hz, 1 H) 2.10 - 2.33 (m, 5 H) 2.25 (s, 6 H) 2.34 - 2.50 (m, 2 H) 2.36 (s, 3 H) 2.63 - 2.74 (m, 2 H) 2.77 - 2.95 (m, 3 H) 3.16 - 3.22 (m, 1 H) 3.19 (s, 3 H) 3.30 - 3.39 (m, 1 H) 3.33 (s, 3 H) 3.40 - 3.49 (m, 1 H) 3.53 - 3.67 (m, 2 H) 4.09 - 4.16 (m, 1 H) 4.32 - 4.44 (m, 2 H) 4.58 - 4.70 (m, 2 H) 4.88 (d, J=4.94 Hz, 1 H) 7.22 - 7.38 (m, 5 H)
453			849.8	(500 MHz):0.81 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.06 - 1.35 (m, 20 H) 1.49 - 1.93 (m, 5 H) 2.09 - 2.53 (m, 24 H) 2.63 - 2.71 (m, 1 H) 2.74 - 2.94 (m, 3 H) 3.16 - 3.24 (m, 4 H) 3.30 - 3.70 (m, 8 H) 4.08 - 4.17 (m, 1 H) 4.35 - 4.45 (m, 2 H) 4.59 - 4.68 (m, 1 H) 4.86 (d, J=4.11 Hz, 1 H)
454			849.8	(500 MHz): 0.80 (d, J=6.86 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.06 - 1.27 (m, 17 H) 1.32 (s, 3 H) 1.48 - 1.87 (m, 5 H) 1.99 - 2.07 (m, 1 H) 2.10 - 2.53 (m, 23 H) 2.69 - 2.94 (m, 4 H) 3.16 - 3.24 (m, 4 H) 3.31 - 3.70 (m, 8 H) 4.07 - 4.15 (m, 1 H) 4.36 - 4.48 (m, 2 H) 4.58 - 4.69 (m, 1 H) 4.86 (d, J=4.94 Hz, 1 H)
455			927.9	(500 MHz):0.78 - 0.85 (m, 6 H) 0.91 (t, J=7.26 Hz, 3 H) 1.06 - 1.27 (m, 17 H) 1.32 (s, 3 H) 1.50 - 1.87 (m, 4 H) 1.98 - 2.05 (m, 1 H) 2.10 - 2.53 (m, 14 H) 2.60 - 2.66 (m, 1 H) 2.70 - 2.75 (m, 1 H) 2.79 - 2.96 (m, 3 H) 3.02 - 3.06 (m, 3 H) 3.16 - 3.24 (m, 4 H) 3.31 - 3.38 (m, 4 H) 3.41 - 3.67 (m, 3 H) 4.13 - 4.19 (m, 1 H) 4.36 (d, J=7.65 Hz, 1 H) 4.45 (q, 1 H) 4.58 - 4.67 (m, 1 H) 4.74 (d, J=7.26 Hz, 1 H) 4.91 (d, J=4.97 Hz, 1 H) 7.61 (d, J=8.41 Hz, 2 H) 7.92 (d, J=8.41 Hz, 2 H)

[0866] 

[Table 11-44]

456			976.8	(500 MHz):0.78 - 0.85 (m, 6 H) 0.91 (t, J=7.27 Hz, 3 H) 1.06 - 1.27 (m, 17 H) 1.31 (s, 3 H) 1.50 - 1.88 (m, 4 H) 1.96 - 2.04 (m, 1 H) 2.10 - 2.53 (m, 16 H) 2.60 - 2.95 (m, 5 H) 3.04 (s, 3 H) 3.16 - 3.24 (m, 4 H) 3.32 - 3.38 (m, 5 H) 3.41 - 3.50 (m, 1 H) 3.58 - 3.67 (m, 2 H) 4.12 - 4.19 (m, 1 H) 4.36 (d, J=7.40 Hz, 1 H) 4.44 (q, J=6.76 Hz, 1 H) 4.59 - 4.67 (m, 1 H) 4.74 (d, J=7.13 Hz, 1 H) 4.91 (d, J=4.94 Hz, 1 H) 7.59 - 7.63 (m, 1 H) 7.91 (d, J=8.50 Hz, 2 H)
457			897.9	(600 MHz):0.77 - 0.84 (m, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.05 - 1.22 (m, 2 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 (s, 3 H) 1.13 - 1.17 (m, 6 H) 1.18 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.65 (m, 2 H) 1.71 - 1.87 (m, 2 H) 2.11 - 2.20 (m, 3 H) 2.21 - 2.49 (m, 4 H) 2.26 (s, 6 H) 2.36 (s, 3 H) 2.70 - 2.74 (m, 1 H) 2.76 - 2.94 (m, 7 H) 3.17 (s, 3 H) 3.17 - 3.20 (m, 1 H) 3.33 (s, 3 H) 3.40 - 3.48 (m, 2 H) 3.62 (d, J=8.25 Hz, 1 H) 4.06 - 4.12 (m, 1 H) 4.33 - 4.41 (m, 2 H) 4.62 - 4.71 (m, 1 H) 4.84 - 4.88 (m, 1 H) 7.34 (d, J=8.71 Hz, 2 H) 8.15 (d, J=8.71 Hz, 2 H)
458			927.6	(600 MHz):0.77 - 0.84 (m, 6 H) 0.91 (t, J=7.57 Hz, 3 H) 1.04 - 1.35 (m, 20 H) 1.49 - 1.94 (m, 5 H) 2.10 - 2.52 (m, 14 H) 2.67 - 2.94 (m, 6 H) 3.16 - 3.25 (m, 5 H) 3.29 - 3.47 (m, 5 H) 3.59 - 3.66 (m, 3 H) 3.76 - 3.78 (m, 1 H) 4.08 - 4.15 (m, 1 H) 4.33 - 4.43 (m, 2 H) 4.58 - 4.68 (m, 1 H) 4.84 (d, J=5.04 Hz, 1 H) 7.36 (d, J=8.71 Hz, 2 H) 8.14 - 8.16 (m, 2 H)
459				(600 MHz):0.81 (d, J=7.34 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.05 (s, 3 H) 1.06 - 1.26 (m, 2 H) 1.10 (d, J=7.34 Hz, 3 H) 1.15 - 1.20 (m, 9 H) 1.30 - 1.35 (m, 6 H) 1.50 - 1.70 (m, 3 H) 1.71 - 1.79 (m, 1 H) 1.79 - 1.86 (m, 1 H) 2.09 - 2.18 (m, 1 H) 2.21 - 2.45 (m, 4 H) 2.27 (s, 6 H) 2.37 (s, 3 H) 2.46 - 2.61 (m, 3 H) 2.63 - 2.76 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.88 - 2.93 (m, 1 H) 2.99 - 3.08 (m, 1 H) 3.17 - 3.32 (m, 2 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.33 - 3.50 (m, 3 H) 3.60 - 3.67 (m, 1 H) 3.69 (d, J=8.71 Hz, 1 H) 3.90 (s, 3 H) 4.03 - 4.09 (m, 1 H) 4.21 - 4.27 (m, 1 H) 4.33 (d, J=7.34 Hz, 1 H) 4.39 - 4.45 (m, 1 H) 4.58 - 4.67 (m, 2 H) 4.81 (s, 1 H) 4.95 (d, J=4.59 Hz, 1 H) 6.93 (d, J=8.25 Hz, 1 H) 6.94 - 6.98 (m, 1 H) 7.22 - 7.30 (m, 2 H)
460				(600 MHz): 0.83 (d, J=6.42 Hz, 6 H) 0.90 (t, J=7.34 Hz, 3 H) 1.02 (t, J=7.11 Hz, 3 H) 1.07 - 1.24 (m, 8 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.26 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.44 - 1.78 (m, 6 H) 1.83 - 1.90 (m, 1 H) 1.93 (d, J=10.09 Hz, 1 H) 2.15 - 2.35 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.41 - 2.63 (m, 7 H) 2.78 - 2.91 (m, 3 H) 3.21 (dd, J=10.09, 7.34 Hz, 1 H) 3.25 (s, 3 H) 3.28 (s, 3 H) 3.37 - 3.45 (m, 5 H) 3.53 (t, J=5.50 Hz, 2 H) 3.66 - 3.70 (m, 1 H) 3.72 (d, J=7.79 Hz, 1 H) 3.98 - 4.04 (m, 1 H) 4.08 - 4.11 (m, 1 H) 4.45 (d, J=6.88 Hz, 1 H) 4.63 - 4.70 (m, 1 H) 4.93 (d, J=5.04 Hz, 1 H)
461			876.9	(500 MHz):0.81 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.27 Hz, 3 H) 1.01 (t, J=7.13 Hz, 3 H) 1.08 (d, J=7.40 Hz, 3 H) 1.07 - 1.12 (m, 1 H) 1.12 (s, 3 H) 1.15 (d, J=7.40 Hz, 3 H) 1.20 (d, J=6.03 Hz, 3 H) 1.22 (d, J=6.31 Hz, 3 H) 1.21 - 1.28 (m, 1 H) 1.34 (s, 3 H) 1.49 - 1.58 (m, 2 H) 1.63 - 1.70 (m, 1 H) 1.71 - 1.79 (m, 1 H) 1.78 - 1.86 (m, 1 H) 2.10 - 2.18 (m, 1 H) 2.18 - 2.25 (m, 1 H) 2.26 - 2.33 (m, 2 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.44 (m, 1 H) 2.52 - 2.65 (m, 7 H) 2.74 - 2.82 (m, 1 H) 2.92 (d, J=13.99 Hz, 1 H) 3.21 (s, 3 H) 3.21 - 3.33 (m, 3 H) 3.26 (s, 3 H) 3.36 - 3.42 (m, 1 H) 3.42 - 3.49 (m, 2 H) 3.54 - 3.58 (m, 2 H) 3.66 (d, J=7.95 Hz, 1 H) 4.07 - 4.13 (m, 1 H) 4.13 - 4.19 (m, 1 H) 4.31 (d, J=7.13 Hz, 1 H) 4.56 - 4.64 (m, 1 H) 4.94 (d, J=4.39 Hz, 1 H) 5.08 - 5.12 (m, 1 H) 5.12 - 5.17 (m, 1 H)

[0867] 

[Table 11-45]

462			940.9	mixture of diastereomers (500 MHz):0.77 - 0.85 (m, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 1.07 (d, J=7.40 Hz, 3 H) 1.12 (d, J=2.19 Hz, 3 H) 1.12 - 1.16 (m, 1 H) 1.15 (d, J=7.40 Hz, 3 H) 1.18 - 1.23 (m, 6 H) 1.20 - 1.27 (m, 1 H) 1.35 (s, 3 H) 1.49 - 1.58 (m, 2 H) 1.59 - 1.68 (m, 1 H) 1.70 - 1.79 (m, 1 H) 1.79 - 1.85 (m, 1 H) 2.16 - 2.30 (m, 3 H) 2.26 (s, 6 H) 2.33 (d, J=15.08 Hz, 1 H) 2.36 (s, 3 H) 2.38 - 2.45 (m, 1 H) 2.48 - 2.57 (m, 1 H) 2.76 - 2.80 (m, 1 H) 2.92 (d, J=14.26 Hz, 1 H) 3.10 - 3.16 (m, 1 H) 3.21 (s, 3 H) 3.24 (d, J=2.47 Hz, 3 H) 3.24 - 3.36 (m, 3 H) 3.37 - 3.52 (m, 4 H) 3.66 (d, J=7.40 Hz, 1 H) 3.82 (s, 3 H) 3.91 - 3.98 (m, 1 H) 4.07 - 4.19 (m, 2 H) 4.28 (d, J=7.13 Hz, 1 H) 4.48 - 4.56 (m, 1 H) 4.56 - 4.64 (m, 1 H) 4.93 (d, J=4.11 Hz, 1 H) 5.24 - 5.31 (m, 1 H) 5.31 - 5.38 (m, 1 H) 6.59 - 6.63 (m, 1 H) 6.64 - 6.69 (m, 1 H) 6.73 - 6.77 (m, 1 H) 6.80 - 6.86 (m, 1 H)
463			997.0	mixture of diastereomers (500 MHz):0.74 - 0.85 (m, 6 H) 0.86 - 0.91 (m, 3 H) 0.90 - 1.01 (m, 3 H) 1.06 - 1.12 (m, 6 H) 1.14 - 1.23 (m, 9 H) 1.15 - 1.19 (m, 1 H) 1.21 - 1.26 (m, 1 H) 1.26 - 1.35 (m, 6 H) 1.51 - 1.59 (m, 2 H) 1.61 - 1.70 (m, 1 H) 1.71 - 1.79 (m, 1 H) 1.80 - 1.86 (m, 1 H) 2.10 - 2.17 (m, 1 H) 2.26 - 2.35 (m, 2 H) 2.28 - 2.31 (m, 6 H) 2.35 - 2.37 (m, 3 H) 2.38 - 2.59 (m, 5 H) 2.76 - 2.83 (m, 1 H) 2.89 (d, J=15.08 Hz, 1 H) 2.93 - 3.06 (m, 1 H) 3.19 - 3.23 (m, 1 H) 3.21 (s, 3 H) 3.27 - 3.28 (m, 3 H) 3.33 - 3.50 (m, 6 H) 3.58 - 3.70 (m, 1 H) 3.69 (d, J=8.23 Hz, 1 H) 3.83 (s, 3 H) 4.03 - 4.12 (m, 1 H) 4.17 - 4.24 (m, 1 H) 4.32 - 4.41 (m, 2 H) 4.60 - 4.65 (m, 1 H) 4.96 (d, J=4.66 Hz, 1 H) 6.86 - 6.89 (m, 1 H) 6.94 (t, J=7.40 Hz, 1 H) 7.20 - 7.26 (m, 2 H)
464			1042.0	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 1.03 - 1.59 (m, 26 H) 1.63 - 1.87 (m, 3 H) 2.10 - 2.47 (m, 8 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.51 - 2.69 (m, 3 H) 2.74 - 2.81 (m, 1 H) 2.89 - 2.97 (m, 1 H) 3.07 - 3.54 (m, 7 H) 3.20 (s, 3 H) 3.24 (s, 3 H) 3.61 - 3.72 (m, 2 H) 4.05 - 4.14 (m, 2 H) 4.28 (d, J=7.26 Hz, 1 H) 4.56 - 4.69 (m, 2 H) 4.93 (d, J=4.20 Hz, 1 H) 4.98 - 5.13 (m, 2 H) 7.60 (d, J=8.79 Hz, 2 H) 8.18 (d, J=8.79 Hz, 2 H)
465			1054.7	(500 MHz):0.55 - 0.64 (m, 1 H) 0.76 - 1.00 (m, 11 H) 0.99 - 1.89 (m, 30 H) 1.98 - 2.48 (m, 6 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.50 - 2.68 (m, 3 H) 2.74 - 2.84 (m, 1 H) 2.87 - 2.97 (m, 1 H) 3.06 - 3.54 (m, 6 H) 3.21 (s, 3 H) 3.25 (s, 3 H) 3.61 - 3.75 (m, 2 H) 4.06 - 4.19 (m, 2 H) 4.30 (d, J=6.88 Hz, 1 H) 4.57 - 4.73 (m, 2 H) 4.83 - 5.10 (m, 3 H) 7.08 (s, 1 H) 7.60 (d, J=8.41 Hz, 2 H) 8.19 (d, J=8.79 Hz, 2 H)

[0868] 

[Table 11-46]

466			956.9	(500 MHz):0.80 (d, J=6.88 Hz, 6 H) 0.88 (t, J=7.26 Hz, 3 H) 1.04 - 1.41 (m, 22 H) 1.47 - 1.87 (m, 8 H) 2.09 - 2.45 (m, 7 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.46 - 2.56 (m, 1 H) 2.73 - 2.94 (m, 2 H) 3.08 - 3.50 (m, 7 H) 3.20 (s, 3 H) 3.25 (s, 3 H) 3.65 - 3.69 (m, 1 H) 4.05 - 4.14 (m, 1 H) 4.15 - 4.21 (m, 1 H) 4.30 (d, J=7.26 Hz, 1 H) 4.57 - 4.65 (m, 1 H) 4.75 - 4.83 (m, 1 H) 4.92 - 5.02 (m, 2 H) 6.00 (s, 1 H) 6.99 - 7.06 (m, 1 H)
467			890.8	(600 MHz):0.77 - 0.83 (m, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 1.03 (t, J=7.11 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.21 (m, 2 H) 1.11 (s, 3 H) 1.15 (d, J=7.79 Hz, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 1.58 (m, 2 H) 1.61 - 1.71 (m, 3 H) 1.71 - 1.78 (m, 1 H) 1.79 - 1.87 (m, 1 H) 2.11 - 2.18 (m, 1 H) 2.20 - 2.28 (m, 2 H) 2.29 (s, 6 H) 2.32 - 2.35 (m, 1 H) 2.35 (s, 3 H) 2.37 - 2.45 (m, 1 H) 2.48 - 2.59 (m, 5 H) 2.61 - 2.70 (m, 2 H) 2.76 - 2.82 (m, 1 H) 2.90 (d, J=14.67 Hz, 1 H) 3.21 (s, 3 H) 3.21 - 3.25 (m, 2 H) 3.26 (s, 3 H) 3.32 - 3.48 (m, 4 H) 3.67 (d, J=7.79 Hz, 1 H) 3.79 (t, J=5.27 Hz, 2 H) 4.05 - 4.12 (m, 1 H) 4.13 - 4.18 (m, 1 H) 4.34 (d, J=7.34 Hz, 1 H) 4.58 - 4.65 (m, 1 H) 4.95 (d, J=4.59 Hz, 1 H) 4.96 - 4.99 (m, 1 H) 5.10 - 5.20 (m, 1 H)
468			817.9	(600 MHz):0.81 (d, J=6.88 Hz, 6 H) 0.87 - 0.93 (m, 6 H) 1.06 - 1.29 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.12 (s, 3 H) 1.16 (d, J=7.79 Hz, 3 H) 1.20 (d, J=6.42 Hz, 3 H) 1.22 (d, J=5.96 Hz, 3 H) 1.30 - 1.39 (m, 2 H) 1.32 (s, 3 H) 1.44 - 1.50 (m, 2 H) 1.50 - 1.59 (m, 2 H) 1.60 - 1.69 (m, 1 H) 1.71 - 1.79 (m, 1 H) 1.79 - 1.86 (m, 1 H) 2.08 - 2.18 (m, 1 H) 2.20 - 2.44 (m, 4 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.45 - 2.53 (m, 1 H) 2.76 - 2.83 (m, 1 H) 2.90 (d, J=14.67 Hz, 1 H) 3.13 - 3.19 (m, 2 H) 3.20 - 3.25 (m, 1 H) 3.21 (s, 3 H) 3.27 (s, 3 H) 3.37 - 3.53 (m, 3 H) 3.69 (d, J=7.79 Hz, 1 H) 4.05 - 4.13 (m, 1 H) 4.16 - 4.24 (m, 1 H) 4.25 - 4.31 (m, 1 H) 4.34 (d, J=6.88 Hz, 1 H) 4.56 - 4.66 (m, 1 H) 4.79 (d, J=9.63 Hz, 1 H) 4.96 (d, J=4.59 Hz, 1 H)
469			845.9	(600 MHz):0.78 - 0.85 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.09 - 1.23 (m, 4 H) 1.15 (d, J=7.79 Hz, 3 H) 1.18 (s, 3 H) 1.19 (d, J=6.42 Hz, 3 H) 1.25 (d, J=5.96 Hz, 3 H) 1.26 - 1.35 (m, 7 H) 1.36 - 1.66 (m, 7 H) 1.68 - 1.80 (m, 1 H) 1.80 - 1.90 (m, 1 H) 1.92 (d, J=9.63 Hz, 1 H) 2.19 - 2.26 (m, 3 H) 2.20 (s, 6 H) 2.28 (s, 6 H) 2.32 (d, J=15.13 Hz, 1 H) 2.35 (s, 3 H) 2.40 - 2.46 (m, 1 H) 2.47 - 2.52 (m, 1 H) 2.54 - 2.60 (m, 1 H) 2.76 - 2.83 (m, 2 H) 2.84 - 2.92 (m, 1 H) 3.17 - 3.22 (m, 1 H) 3.24 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.46 (m, 1 H) 3.64 - 3.70 (m, 1 H) 3.71 (d, J=7.34 Hz, 1 H) 3.96 - 4.03 (m, 1 H) 4.08 (s, 1 H) 4.44 (d, J=7.34 Hz, 1 H) 4.65 (s, 1 H) 4.92 (d, J=5.04 Hz, 1 H)
470			1002.1	(600 MHz): 0.81 (d, J=6.42 Hz, 6 H) 0.89 (t, J=7.34 Hz, 3 H) 0.96 (t, J=6.88 Hz, 3 H) 1.06 - 1.28 (m, 2 H) 1.09 (d, J=7.34 Hz, 3 H) 1.16 (d, J=7.34 Hz, 3 H) 1.21 (d, J=6.42 Hz, 3 H) 1.23 (s, 3 H) 1.25 (d, J=6.42 Hz, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.49 - 2.02 (m, 7 H) 2.06 - 2.70 (m, 10 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.73 - 3.34 (m, 6 H) 3.23 (s, 3 H) 3.28 (s, 3 H) 3.37 - 3.46 (m, 2 H) 3.62 - 3.68 (m, 1 H) 3.80 (s, 3 H) 4.09 - 4.23 (m, 2 H) 4.29 - 4.36 (m, 2 H) 4.58 - 4.70 (m, 2 H) 4.96 (d, J=4.59 Hz, 1 H) 6.83 - 6.98 (m, 2 H) 7.17 - 7.34 (m, 2 H)

[0869] 

[Table 11-47]

471			718.5	(300 MHz) : 0.81 - 0.84 (m, 6 H) 0.90 (t, J=7.2 Hz, 3 H) 1.10 (d, J=7.2 Hz, 3 H) 1.16 - 1.26 (m, 13 H) 1.32 (s, 3H) 1.51 - 1.85 (m, 6 H) 2.03 (d, J=15.6 Hz, 1H) 2.14 - 2.57 (m, 15 H) 2.77 - 2.93 (m, 2 H) 3.18 - 3.25 (m, 4 H) 3.33 (s, 3 H) 3.41 - 3.50 (m, 2 H) 3.70 (d, J=7.8 Hz, 1 H) 4.14 (d, J=5.1 Hz, 1 H) 4.46 (d, J=7.2 Hz, 1 H) 4.62 - 4.68 (m, 2 H) 4.96 (d, J=4.8 Hz, 1 H)
472			1073.3	mixture of diastereomers (300 MHz) : 0.82 (d, J=6.87 Hz, 6 H) 0.90 (t, J=7.14 Hz, 3 H) 0.94 - 1.04 (m, 3 H) 1.07 - 1.35 (m, 23 H) 1.49 - 1.90 (m, 5 H) 2.12 - 2.66 (m, 8 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.95 (m, 2 H) 3.16 - 3.50 (m, 9 H) 3.24 (s, 3 H) 3.51 - 3.64 (m, 1 H) 3.71 (d, J=8.24 Hz, 1 H) 3.74 - 3.83 (m, 1 H) 3.89 (s , 3 H) 4.19 - 4.27 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.55 (d, J=9.61 Hz, 1 H) 4.59 - 4.70 (m, 1 H) 4.98 (d, J=4.60 Hz, 1 H) 5.13 (s, 2 H) 5.18 - 5.29 (m, 1 H) 6.74 (d, J=8.24 Hz, 1 H) 6.82 (d, J=8.51 Hz, 1 H) 6.86 (s, 1 H) 7.27 - 7.46 (m, 5 H)
473			1149.4	mixture of diastereomers (300 MHz) : 0.82 (d, J=6.86 Hz, 6 H) 0.84 -0.94 (m, 3 H) 1.05 -1.32 (m, 23 H) 1.41 - 1.91 (m, 8 H) 2.11 - 2.76 (m, 8 H) 2.21 (s, 3 H) 2.23 (s, 3 H) 2.37 (s, 3 H) 2.76 - 2.86 (m, 1 H) 2.89 (d, J=15.38 Hz, 1 H) 2.99 -3.58 (m, 10 H) 3.23 (s , 3 H) 3.67 - 3.77 (m, 1 H) 4.21 - 4.54 (m, 4 H) 4.58 - 4.73 (m, 2 H) 4.93 - 4.99 (m, 1 H) 5.05 - 5.13 (m, 4 H) 5.43 - 5.69 (m, 1 H) 6.59 (d, J=8.24 Hz, 2 H) 7.05 - 7.13 (m, 1 H) 7.27 - 7.44 (m, 10 H)
474			1078.4	mixture of diastereomers (300 MHz) : 0.83 (d, J=6.87 Hz, 6 H) 0.91 (t, J=7.41 Hz, 3 H) 0.94 - 1.04 (m, 3 H) 1.08 - 1.47 (m, 26 H) 1.56 - 1.91 (m, 11 H) 2.12 - 2.68 (m, 12 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.77 - 2.95 (m, 2 H) 3.15 -3.65 (m, 7 H) 3.24 (s , 3 H) 3.34 (s , 3 H) 3.53 (s , 2 H) 3.72 (d, J=8.24 Hz, 1 H) 3.76 - 3.88 (m, 1 H) 4.00 (q, J=6.87 Hz, 2 H) 4.19 - 4.28 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.56 (d, J=9.62 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.98 (d, J=4.67 Hz, 1 H) 5.37 - 5.45 (m, 1 H) 6.77 (d, J=8.24 Hz, 1 H) 7.09 (d, J=7.97 Hz, 1 H) 7.27 - 7.29 (m, 1 H)
475			1006.3	mixture of diastereomers (300 MHz) : 0.82 (d, J=6.87 Hz, 6 H) 0.91 (t, J=7.42 Hz, 3 H) 0.95 - 1.35 (m, 26 H) 1.47 - 1.93 (m, 5 H) 2.11 - 2.64 (m, 8 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.95 (m, 2 H) 3.17 - 3.64 (m, 7 H) 3.24 (s , 3 H) 3.35 (s , 3 H) 3.69 (s , 2 H) 3.72 (d, J=8.51 Hz, 1 H) 3.76 - 3.85 (m, 1 H) 3.86 (s , 3 H) 4.21 - 4.29 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.55 (d, J=9.89 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.98 (d, J=4.39 Hz, 1 H) 5.17 - 5.25 (m, 1 H) 6.83 (d, J=8.52 Hz, 1 H)7.21-7.28(m,2H)

[0870] 

[Table 11-48]

476			942.3	mixture of diastereomers (300 MHz) : 0.83 (d, J=6.87 Hz, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 0.98 - 1.35 (m, 26 H) 1.47 - 1.94 (m, 5 H) 2.12 - 2.48 (m, 8 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.51 - 2.67 (m, 3 H) 2.76 - 2.95 (m, 2 H) 3.14 -3.48 (m, 15 H) 3.24 (s , 3 H) 3.51 - 3.63 (m, 1 H) 3.72 (d, J=8.24 Hz, 1 H) 3.71 - 3.89 (m, 1 H) 4.20 - 4.28 (m, 1 H) 4.34 - 4.48 (m, 2 H) 4.55 (d, J=9.89 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.98 (d, J=4.67 Hz, 1 H) 5.13 - 5.27 (m, 1 H) 8.10 (s, 1 H)
477			1080.4	mixture of diastereomers (300 MHz) : 0.82 (d, J=6.87 Hz, 6 H) 0.90 (t, J=7.41 Hz, 3 H) 0.94 - 1.03 (m, 3 H) 1.07 - 1.36 (m, 23 H) 1.40 (t, J=6.87 Hz, 3 H) 1.47 - 1.90 (m, 5 H) 2.12 - 2.67 (m, 12 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.87 (m, 1 H) 2.89 (d, J=15.66 Hz, 1 H) 3.14 - 3.43 (m, 6 H) 3.23 (s , 3 H) 3.34 (s , 3 H) 3.53 - 3.64 (m, 1 H) 3.56 (s , 2 H) 3.67 - 3.88 (m, 5 H) 4.01 (q, J=6.86 Hz, 2 H) 4.20 - 4.29 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.56 (d, J=9.89 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.98 (d, J=4.39 Hz, 1 H) 5.31 - 5.43 (m, 1 H) 6.78 (d, J=8.51 Hz, 1 H) 7.11 (d, J=8.24 Hz, 1 H) 7.23 - 7.27 (m, 1 H)
478			982	mixture of diastereomers (300 MHz) : 0.83 (d, J=6.87 Hz, 6 H) 0.90 (t, J=7.41 Hz, 3 H) 0.99 - 1.39 (m, 26 H) 1.54 - 1.89 (m, 5 H) 2.11 - 2.69 (m, 8 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.95 (m, 2 H) 3.17 - 3.43 (m, 9 H) 3.24 (s , 3 H) 3.54 - 3.67 (m, 1 H) 3.72 (d, J=7.97 Hz, 1 H) 3.85 (s , 2 H) 4.04 - 4.12 (m, 1 H) 4.19 - 4.27 (m, 1 H) 4.35 - 4.48 (m, 2 H) 4.56 (d, J=9.88 Hz, 1 H) 4.60 - 4.69 (m, 1 H) 4.98 (d, J=4.67 Hz, 1 H) 5.18 - 5.28 (m, 1 H) 6.71 (d, J=3.30Hz, 1 H) 6.87 - 6.90 (m, 1 H)
479			953	mixture of diastereomers (300 MHz) : 0.83 (d, J=6.60 Hz, 6 H) 0.90 (t, J=7.15 Hz, 3 H) 0.97 - 1.05 (m, 3 H) 1.07 - 1.29 (m, 17 H) 1.31 (s, 3 H) 1.37 (d, J=6.59 Hz, 3 H) 1.55 - 1.93 (m, 5 H) 2.10 - 2.75 (m, 14 H) 2.21 (s, 3 H) 2.29 (s, 3 H) 2.36 (s, 3 H) 2.77 - 2.95 (m, 2 H) 2.98 -3.75 (m, 15 H) 4.14 - 4.54 (m, 4 H) 4.59 - 4.70 (m, 1 H) 4.95 - 5.00 (m, 1 H) 5.08 - 5.68 (m, 1 H) 8.30 - 8.48 (m, 2 H)
480			938	mixture of diastereomers (300 MHz) : 0.83 (d, J=7.15 Hz, 6 H) 0.91 (t, J=6.59 Hz, 3 H) 0.96 - 1.05 (m, 3 H) 1.07 - 1.37 (m, 24 H) 1.49 - 1.91 (m, 5 H) 2.08 - 2.66 (m, 8 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.95 (m, 2 H) 3.18 -3.43 (m, 9 H) 3.24 (s , 3 H) 3.53 - 3.65 (m, 1 H) 3.72 (d, J=7.97 Hz, 1 H) 3.79 - 3.91 (m, 1 H) 4.19 - 4.27 (m, 1 H) 4.36 - 4.48 (m, 2 H) 4.52 - 4.59 (m, 1 H) 4.59 - 4.69 (m, 1 H) 4.98 (d, J=4.67 Hz, 1 H) 5.14 - 5.23 (m, 1 H) 7.25 - 7.27 (m, 2 H) 8.53 (d, J=6.04 Hz, 2 H)

[0871] 

[Table 11-49]

481			969.4	mixture of diastereomers (300 MHz) : 0.83 (d, J=6.87 Hz, 6 H) 0.90 (t, J=7.42 Hz, 3 H) 0.96 - 1.07 (m, 3 H) 1.08 - 1.35 (m, 20 H) 1.31 (s, 3 H) 1.41 - 1.48 (m, 3 H) 1.50 - 1.95 (m, 5 H) 2.11 - 2.64 (m, 11 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.75 - 2.88 (m, 1 H) 2.89 (d, J=14.56 Hz, 1 H) 3.14 -3.48 (m, 9 H) 3.24 (s , 3 H) 3.52 - 3.67 (m, 1 H) 3.71 (d, J=7.97 Hz, 1 H) 3.81 - 3.93 (m, 1 H) 4.01 - 4.10 (m, 2 H) 4.17 - 4.25 (m, 1 H) 4.34 - 4.45 (m, 1 H) 4.46 (d, J=7.42 Hz, 1 H) 4.51 - 4.58 (m, 1 H) 4.59 - 4.71 (m, 1 H) 4.98 (d, J=4.40 Hz, 1 H) 5.18 - 5.28 (m, 1 H) 7.15 - 7.18 (m, 1 H)
482			833	(400 MHz) : 0.81 - 0.89 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.11 - 1.28 (m, 18 H) 1.32 (s, 3 H) 1.49 - 1.67 (m, 8 H) 2.17 - 2.43 (m, 15 H) 2.64 - 2.66 (m, 1 H) 2.73 (t, J=6.7 Hz, 1 H) 2.80 - 2.83 (m, 1 H) 2.90 (d, J=15.1 Hz, 1 H) 3.20 - 3.23 (m, 6 H) 3.34 (s, 3 H) 3.39 (m, 1 H) 3.56 (m, 1 H) 3.70 - 3.75 (m, 3 H) 4.22 (m, 1 H) 4.35 - 4.45 (m, 2 H) 4.54 (d, J=10.0 Hz, 1 H) 4.64 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H) 5.07 (m, 1 H)
483			806 FAB MASS	(400 MHz) : 0.82 - 0.89 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.01 - 1.24 (m, 16 H) 1.32 (s, 3 H) 1.53 - 2.09 (m, 6 H) 2.18 - 2.45 (m, 14 H) 2.58 - 2.62 (m, 1 H) 2.78 - 2.92 (m, 2 H) 3.20 - 3.23 (m, 4 H) 3.34 (s, 3 H) 3.36 - 3.39 (m, 3 H) 3.56 - 3.59 (m, 1 H) 3.65 - 3.75 (m, 3 H) 4.21 (m, 1 H) 4.36 - 4.45 (m, 2 H) 4.54 (d, J=9.8.Hz, 1 H) 4.64 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H) 5.39 (m, 1 H)
484			820.3	(400 MHz) : 0.82 - 0.83 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.12 - 1.27 (m, 16 H) 1.32 (s, 3 H) 1.52 - 1.76 (m, 6 H) 2.19 - 2.44 (m, 14 H) 2.60 (m, 1 H) 2.80 - 2.92 (m, 2 H) 3.17 - 3.24 (m, 4 H) 3.34 - 3.35 (m, 7 H) 3.37 - 3.47 (m, 4 H) 3.56 - 3.59 (m, 1 H) 3.70 (d, J=8.1 Hz, 1 H) 4.21 (m, 1 H) 4.34 - 4.46 (m, 2 H) 4.54 (d, J=9.8 Hz, 1 H) 4.65 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H) 5.23 (m, 1 H)
485			820.3	(400 MHz): 0.82 - 0.83 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 1.09 - 1.26 (m, 16 H) 1.33 (s, 3 H) 1.52 - 1.85 (m, 6 H) 2.15 - 2.67 (m, 15 H) 2.82 - 2.99 (m, 5 H) 3.10 (d, J=7.6 Hz, 1 H) 3.23 (s, 3 H) 3.42 - 3.78 (m, 7 H) 4.10 (m, 1 H) 4.41 - 4.47 (m, 2 H) 4.58 - 4.64 (m, 2 H) 4.97 (d, J=4.6 Hz, 1 H)

[0872] 

[Table 11-50]

486			830.3	(400 MHz) : 0.82 - 0.84 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 1.10 - 1.28 (m, 16 H) 1.31 (s, 3 H) 1.50 - 1.64 (m, 10 H) 1.74 (m, 1 H) 1.88 (m, 1 H) 2.14 - 2.47 (m, 14 H) 2.56 (m, 1 H) 2.80 - 2.93 (m, 2 H) 3.22 - 3.27 (m, 4 H) 3.33 (s, 3 H) 3.44 (m, 5 H) 3.63 (m, 1 H) 3.70 (d, J=6.8 Hz, 1 H) 4.07 (d, J=4.6 Hz, 1 H) 4.39 (m, 1 H) 4.55 - 4.59 (m, 2 H) 4.67 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H)
487			832.3	(400 MHz): 0.82 - 0.84 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 1.10 - 1.31 (m, 19 H) 1.50 - 1.64 (m, 4 H) 1.75 (m, 1 H) 1.87 (m, 1 H) 2.23 - 2.37 (m, 4 H) 2.42 (s, 3 H) 3.41 - 3.71 (m, 8 H) 4.10 (d, J=4.4 Hz, 1 H) 4.40 (m, 1 H) 4.53 - 4.59 (m, 2 H) 4.64 (m, 1 H) 4.98 (d, J=4.9 Hz, 1 H)
488			818.3	(400 MHz): 0.82 - 0.83 (m, 6 H) 0.86 - 0.92 (m, 6 H) 1.09 - 1.37 (m, 23 H) 1.45 - 1.93 (m, 6 H) 2.14 - 2.44 (m, 14 H) 2.60 (m, 1 H), 2.80 (m, 1 H) 2.90 (d, J=15.4 Hz, 1 H) 3.19 - 3.24 (m, 6 H) 3.34 (s, 3 H) 3.40 (d, J=8.3 Hz, 1 H) 3.55 (m, 1 H) 3.71 (d, J=8.3 Hz, 1 H) 4.22 (m, 1 H) 4.34 - 4.44 (m, 2 H) 4.55 (d, J=9.8 Hz, 1 H) 4.64 (m, 1 H) 4.86 (t, J=5.5 Hz, 1 H) 4.98 (d, J=4.6 Hz, 1 H)
489			776	(400 MHz): 0.82 - 0.83 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.12 - 1.27 (m, 16 H) 1.32 (s, 3 H) 1.50 - 1.88 (m, 6 H) 2.14 - 2.43 (m, 14 H) 2.59 (m, 1 H) 2.80 - 2.84 (m, 4 H) 2.90 (d, J=14.2 Hz, 1 H) 3.19 - 3.23 (m, 4 H) 3.34 (s, 3 H) 3.39 (d, J=8.6 Hz, 1 H) 3.55 (m, 1 H) 3.70 (d, J=8.3 Hz, 1 H), 4.22 (m, 1 H), 4.34 - 4.44 (m, 2 H) 4.56 (d, J=9.8 Hz, 1 H) 4.64 (m, 1 H) 4.80 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H)
490			805	(400 MHz) : 0.83 (d, J=6.82 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.08 - 1.28 (m, 2 H) 1.13 (d, J=7.31 Hz, 3H) 1.17 (s, 3 H) 1.18 (d, J=8.04 Hz, 6 H) 1.20 (d, J=6.09 Hz, 3 H) 1.32(s, 3 H) 1.50 - 1.90 (m, 8 H) 2.10 - 2.46 (m, 6 H) 2.32 (s, 6 H) 2.37 (s, 3 H) 2.58 - 2.67 (m, 1 H) 2.75 -2.95 (m, 4 H) 3.15 - 3.31 (m, 3 H) 3.24 (s, 3 H) 3.34 (s, 3 H) 3.40 (d, J=6.33 Hz, 1 H) 3.54 - 3.63 (m, 1 H) 3.71 (d, J=8.04 Hz, 1 H) 4.16 - 4.25 (m, 1 H) 4.34 - 4.44 (m, 1 H) 4.45 (d, J=7.06 Hz, 1 H) 4.54 (d, J=9.74 Hz, 1 H) 4.60 - 4.70 (m, 1 H) 4.98 (d, J=4.78 Hz, 1 H) 5.31 (t, J=5.60 Hz, 1 H)

[0873] 

[Table 11-51]

491			819	(400 MHz) : 0.82 (d, J=6.82 Hz, 6 H) 0.95 (t, J=7.31 Hz, 3 H) 1.08 - 1.26 (m, 2 H) 1.12 (d, J=7.31 Hz, 3H) 1.16 (s, 3 H) 1.17 (d, J=9.01 Hz, 6 H) 1.21 (d, J=6.33 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.92 (m, 10 H) 2.10 - 2.48 (m, 6 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.55 - 2.64 (m, 1 H) 2.78 (t, J=6.58 Hz, 2 H) 2.82 (dd, J=5.36 .7.31 Hz, 1 H) 2.90 (d, J=15.10 Hz, 1 H) 3.18 - 3.26 (m, 1 H) 3.24 (s , 3 H) 3.28 - 3.36 (m, 2 H) 3.34 (s, 3 H) 3.40 (d, J=6.57 Hz, 1 H) 3.52 - 3.62 (m, 1 H) 3.71 (d, J=8.29 Hz, 1 H) 4.16 - 4.27 (m, 1 H) 4.32 - 4.43 (m, 1 H) 4.44 (d, J=7.06 Hz, 1 H) 4.55 (d, J=9.74 Hz, 1 H) 4.59 - 4.69 (m, 1 H) 4.98 (d, J=4.63 Hz, 1 H) 5.28 (t, J=5.60 Hz, 1 H)
492			833	(400 MHz) : 0.82 (d, J=6.82 Hz, 6 H) 0.90 (t, J=7.31 Hz, 3 H) 1.08 - 1.24 (m, 2 H) 1.12 (d, J=7.31 Hz, 3H) 1.17 (s, 3 H) 1.18 (d, J=6.09 Hz, 6 H) 1.19 (d, J=7.31 Hz, 3 H) 1.32 (s, 3 H) 1.45 - 1.95 (m, 6 H) 2.12 - 2.35 (m, 4 H) 2.21 (s, 6 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.37 - 2.48 (m, 4 H) 2.55 - 2.65 (m, 1 H) 2.76 - 2.86 (m, 1 H) 2.90 (d, J=14.8 Hz, 1 H) 3.17 - 3.22 (m, 3 H) 3.24 (s , 3 H) 3.34 (s, 3 H) 3.36 - 3.50 (m, 1 H) 3.55 - 3.65 (m, 1 H) 3.71 (d, J=8.04 Hz, 1 H) 4.14 - 4.23 (m, 1 H) 4.33 - 4.43 (m, 1 H) 4.46 (d, J=7.06 Hz, 1 H) 4.54 (d, J=9.75 Hz, 1 H) 4.60 - 4.70 (m, 1 H) 4.98 (d, J=4.63 Hz, 1 H) 5.39 (t, J=4.87 Hz, 1 H)
493			815	(400 MHz): 0.82 (d, J=6.82 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.08 - 1.24 (m, 2 H) 1.13 (d, J=7.31 Hz, 3H) 1.16 (s, 3 H) 1.18 (d, J=5.11 Hz, 6 H) 1.21 (d, J=6.09 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.95 (m, 6 H) 2.11 - 2.48 (m, 5 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.54 - 2.62 (m, 1 H) 2.64 (t, J=6.33 Hz, 2 H) 2.78 - 2.86 (m, 1 H) 2.90 (d, J=14.61 Hz, 1 H) 3.16 - 3.24 (m, 2 H) 3.23 (s , 3 H) 3.34 (s, 3 H) 3.36 - 3.61 (m, 4 H) 3.70 (d, J=8.04 Hz, 1 H) 4.18 - 4.27 (m, 1 H) 4.35 - 4.45 (m, 2 H) 4.55 (d, J=9.74 Hz, 1 H) 4.58 - 4.70 (m, 1 H) 4.99 (d, J=4.63 Hz, 1 H) 5.38 (t, J=6.33 Hz, 1 H)
494			820	(400 MHz) : 0.82 (d, J=6.82 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.07 - 1.29 (m, 2 H) 1.12 (d, J=7.06 Hz, 3H) 1.17 (s, 3 H) 1.18 (d, J=7.80 Hz, 6 H) 1.20 (d, J=6.82 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.91 (m, 8 H) 2.10 - 2.48 (m, 4 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.54 - 2.67 (m, 1 H) 2.75 - 2.87 (m, 1 H) 2.90 (d, J=14.61 Hz, 1 H) 3.12 - 3.27 (m, 2 H) 3.23 (s , 3 H) 3.31 - 3.48 (m, 3 H) 3.34 (s, 3 H) 3.52 - 3.75 (m, 4 H) 4.16 - 4.26 (m, 1 H) 4.33 - 4.42 (m, 1 H) 4.44 (d, J=7.07 Hz, 1 H) 4.55 (d, J=9.74 Hz, 1 H) 4.58 - 4.69 (m, 1 H) 4.98 (d, J=4.63 Hz, 1 H) 5.19 (t, J=4.87 Hz, 1 H)
495			834	(400 MHz) : 0.82 (d, J=6.81 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.08 - 1.28 (m, 2 H) 1.12 (d, J=7.31 Hz, 3H) 1.16 (s, 3 H) 1.17 (d, J=6.33 Hz, 6 H) 1.19 (d, J=7.06 Hz, 3 H) 1.39 (s, 3 H) 1.50 - 1.72 (m, 10 H) 2.10 - 2.21 (m, 1 H) 2.22 - 2.47 (m, 3 H) 2.32 (s, 6 H) 2.37 (s, 3 H) 2.54 - 2.66 (m, 1 H) 2.77 - 2.87 (m, 1 H) 2.91 (d, J=14.61 Hz, 1 H) 3.18 - 3.29 (m, 4 H) 3.23 (s , 3 H) 3.34 (s, 3 H) 3.36 - 3.50 (m, 2 H) 3.51 - 3.61 (m, 1 H) 3.65 - 3.73 (m, 3 H) 4.18 - 4.26 (m, 1 H) 4.33 - 4.43 (m, 3 H) 4.43 (d, J=7.31 Hz, 1 H) 4.55 (d, J=9.74 Hz, 1 H) 4.59 - 4.61 (m, 1 H) 4.98 (d, J=4.63 Hz, 1 H) 5.04 (t, J=4.87 Hz, 1 H)

[0874] 

[Table 11-52]

496			762	(400 MHz) : 0.82 (d, J=7.06 Hz, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.06 - 1.25 (m, 2 H) 1.13 (d, J=7.30 Hz, 3H) 1.18 (s, 3 H) 1.18 (d, J=8.28 Hz, 3 H) 1.21 (d, J=6.09 Hz, 6 H) 1.32 (s, 3 H) 1.49 - 1.93 (m, 7 H) 2.16 (d, J=14.37 Hz, 1 H) 2.21 - 2.49 (m, 3 H) 2.31 (s, 6 H) 2.37 (s, 3 H) 2.56 - 2.64 (m, 1 H) 2.76 - 2.87 (m, 1 H) 2.90 (d, J=15.10 Hz, 1 H) 3.15 - 3.26 (m, 2 H) 3.24 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.50 - 3.61 (m, 1 H) 3.71 (d, J=8.04 Hz, 1 H) 4.19 - 4.28 (m, 1 H) 4.36 - 4.44 (m, 1 H) 4.43 (d, J=7.07 Hz, 1 H) 4.54 (d, J=9.75 Hz, 1 H) 4.59 - 4.93 (m, 3 H) 4.98 (d, J=4.63 Hz, 1 H)
497			790	(300 MHz) : 0.78 - 0.88 (m, 6 H) 0.90 (t, J=7.42 Hz, 3 H) 1.09 - 1.27 (m, 11 H) 1.11 (d, J=5.76 Hz, 3 H) 1.12 (s, 3 H) 1.31 (s, 3 H) 1.44 - 1.95 (m, 7 H) 2.12 - 2.48 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.77 - 2.95 (m, 2 H) 2.92 (s, 3 H) 2.94 (s , 3 H) 3.15 - 3.27 (m, 2 H) 3.24 (s , 3 H) 3.33 (s, 3 H) 3.36 - 3.54 (m, 1 H) 3.58 - 3.69 (m, 1 H) 3.71 (d, J=7.41Hz, 1 H) 4.08 (d, J=5.50 Hz, 1 H) 4.35 - 4.48 (m, 1 H) 4.54 (d, J=9.62 Hz, 1 H) 4.56 (d, J=7.14 Hz, 1 H) 4.61 - 4.71 (m, 1 H) 4.97 (d, J=4.67 Hz, 1 H)
498			831.4	(400 MHz) : 0.83 (d, J=6.33 Hz, 6 H) 0.90 (t, J=7.31 Hz, 3 H) 1.07 - 1.28 (m, 11 H) 1.11 (d, J=8.28 Hz, 3H) 1.12 (s, 3 H) 1.31(s, 3 H) 1.49 - 1.94 (m, 8 H) 2.13 - 2.48 (m, 5 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.48 - 2.58 (m, 1 H) 2.73 -2.95 (m, 6 H) 3.16 - 3.27 (m, 2 H) 3.24 (s , 3 H) 3.33 (s, 3 H) 3.34 - 3.65 (m, 2 H) 3.70 (d, J=7.06 Hz, 1 H) 4.03 - 4.13 (m, 1 H) 4.35 - 4.45 (m, 1 H) 4.52 - 4.60 (m, 2 H) 4.60 - 4.70 (m, 1 H) 4.98 (d, J=4.38 Hz, 1 H)
499			956.6	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.01 - 1.03 (m, 3 H) 1.05 - 1.37 (m, 22 H) 1.52 - 1.85 (m, 6 H) 2.06 - 2.44 (m, 22 H) 2.57 - 2.92 (m, 5 H) 3.15 - 3.41 (m, 9 H) 3.59 (m, 1 H) 3.72 (d, J= 8.1 Hz, 1 H) 3.93 (q, J= 7.1 Hz, 1H) 4.23 (m, 1 H) 4.38 - 4.48 (m, 2 H) 4.55 - 4.59 (m, 1 H) 4.65 (m, 1 H) 4.99 (d, J=4.9 Hz, 1 H) 5.30 - 5.35 (m, 1 H)
500			1005.5	mixture of diastereomers, (400 MHz) : 0.82 - 0.83 (m, 6 H) 0.92 (t, J=7.3 Hz, 3 H) 0.99 - 1.32 (m, 22 H) 1.40 (d, J= 6.8 Hz) 1.52 - 1.85 (m, 6 H) 2.14 - 2.67 (m, 19 H) 2.80 - 2.92 (m, 2 H) 3.19 - 3.39 (m, 9 H) 3.56 (m, 1 H) 3.71 (d, J= 8.3 Hz, 1 H) 3.97 (q, J= 7.3 Hz, 1 H) 4.25 (m, 1 H) 4.36 - 4.45 (m, 2 H) 4.54 (d, J=9.8 Hz, 1 H) 4.64 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 5.18 - 5.20 (m, 1 H) 7.52 - 7.59 (m, 3 H) 7.73 (m, 1 H) 9.13 (m, 1 H)

[0875] 

[Table 11-53]

501			969.6	mixture of diastereomers, (400 MHz): 0.82 - 0.83 (m, 6 H) 0.89 - 0.97 (m, 6 H) 1.12 - 1.33 (m, 22 H) 1.52 - 1.64 (m, 6 H) 2.19 - 2.71 (m, 25 H) 2.80 - 2.91 (m, 2 H) 3.19 - 3.24 (m, 6 H) 3.34 - 3.40 (m, 4 H) 3.51 - 3.72 (m, 6 H) 4.22 (m, 1 H) 4.39 - 4.55 (m, 2 H) 4.65 (m, 1 H) 4.98 (d, J=4.6 Hz, 1 H) 5.11 - 5.13 (m, 1 H)
502			1022.7	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 0.95 - 1.01 (m, 3 H) 1.11 - 1.33 (m, 22 H) 1.47 - 1.64 (m, 6 H) 2.25 - 2.62 (m, 19 H) 2.79 - 2.91 (m, 2 H) 3.13 - 3.16 (m, 4 H) 3.20 - 3.24 (m, 6 H) 3.31 - 3.39 (m, 4 H) 3.61 (m, 1 H) 3.72 (d, J= 8.1 Hz, 1 H) 3.76 - 3.87 (m, 5 H) 4.22 (m, 1 H) 4.37 - 4.48 (m, 2 H) 4.55 (d, J=9.8 Hz, 1 H) 4.65 (m, 1 H) 4.98 (d, J=4,6 Hz, 1 H) 5.27 - 5.30 (m, 1 H) 6.85 (d, J=8.6 Hz, 2 H) 7.19 (d, J=8.6 Hz, 2 H)
503			1086.7	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 0.98 - 1.02 (m, 3 H) 1.10 - 1.32 (m, 19 H) 1.37 (d, J=6.8 Hz, 3 H) 1.50 - 1.65 (m, 6 H) 2.25 - 2.66 (m, 19 H) 2.81 - 2.91 (m, 2 H) 3.01 (m, 4 H) 3.20 - 3.40 (m, 10 H) 3.58 (m, 1 H) 3.71 - 3.77 (m, 5 H) 3.93 (d, J=6.8 Hz, 1 H) 4.25 (m, 1 H) 4.37 - 4.45 (m, 2 H) 4.56 (d, J=9.8 Hz, 1 H) 4.65 (m, 1 H) 4.99 (d, J=4.4 Hz, 1 H) 5.19 (m, 1 H) 7.51 (d, J=8.3 Hz, 2 H) 7.69 (d, J=8.3 Hz, 2 H)
504			969.6	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 0.99 - 1.42 (m, 22 H) 1.52 - 1.64 (m, 6 H) 2.09 - 2.60 (m, 22 H) 2.81 - 2.92 (m, 2 H) 3.19 - 3.24 (m, 6 H) 3.34 - 3.39 (m, 4 H) 3.58 (m, 1 H) 3.71 (d, J=7.8 Hz, 1 H) 3.82 (q, J=7.1 Hz, 1 H) 4.05 - 4.11 (m, 2 H) 4.22 (m, 1 H) 4.36 - 4.46 (m, 2 H) 4.54 (dd, J=9.8 Hz, J=2.0 Hz, 1 H) 4.65 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 5.16 - 5.25 (m, 1 H)
505			1095.6	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 0.95 - 0.99 (m, 3 H) 1.10 - 1.32 (m, 22 H) 1.52 - 1.64 (m, 6 H) 2.15 - 2.62 (m, 19 H) 2.81 - 2.92 (m, 2 H) 3.19 - 3.24 (m, 6 H) 3.31 - 3.39 (m, 4 H) 3.60 (m, 1 H) 3.71 - 3.78 (m, 5 H) 3.85 (s, 3 H) 4.23 (m, 1 H) 4.37 - 4.57 (m, 5 H) 4.65 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 5.30 - 5.35 (m, 1 H) 6.62 (d, J=8.5 Hz, 1 H) 7.20 (d, J=8.5 Hz, 1 H), 7.27 (brs, 1 H)

[0876] 

[Table 11-54]

506			1038.6	mixture of diasteremers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.12 - 1.32 (m, 28 H) 1.52 - 1.67 (m, 6 H) 2.15- 2.43 (m, 14 H) 2.56 - 2.62 (m, 3 H) 2.80 - 2.91 (m, 2 H) 3.16 - 3.27 (m, 6 H) 3.30 - 3.44 (m, 8 H) 3.59 (m, 1 H) 3.69 - 3.73 (m, 2 H) 4.22 (m, 1 H) 4.35 - 4.47 (m, 2 H) 4.53 - 4.56 (dd, J=9.8 Hz, J=1.7 Hz, 1 H) 4.65 (m, 3 H) 4.98 (d, J=4.6 Hz, 1 H) 5.27 - 5.31 (m, 1 H) 6.89 (dd, J=8.6 Hz, J=2.0 Hz, 2 H) 7.18 (d, J=8.6 Hz, 1 H)
507			1036.6	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.12 - 1.32 (m, 25 H) 1.52 - 2.01 (m, 10 H) 2.25 - 2.44 (m, 16 H) 2.59 (m, 3 H) 2.81 - 2.91 (m, 2 H) 3.20 - 3.73 (m, 17 H) 4.22 (m, 1 H) 4.37 - 4.46 (m, 2 H) 4.53 - 4.64 (m, 4 H) 4.98 (d, J=4.6 Hz, 1 H) 5.29 - 5.31 (m, 1 H) 6.89 (dd, J=8.6 Hz, J=1.9 Hz, 2 H) 7.18 (d, J=8.6 Hz, 1 H)
508			977.5	mixture of diastereomers, (400 MHz) : 0.82 - 0.84 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.12 - 1.32 (m, 19 H) 1.37 (d, J=6.6 Hz, 3 H) 1.52 - 1.73 (m, 6 H) 2.28 - 2.44 (m, 14 H) 2.55 - 2.69 (m, 3 H) 2.81 - 2.92 (m, 2 H) 3.22 - 3.39 (m, 10 H) 3.58 (m, 1 H) 3.71 (d, J=8.1 Hz, 1 H) 3.87 (q, J=6.4 Hz, 1 H) 4.23 (m, 1 H) 4.37 - 4.45 (m, 2 H) 4.55 (dd, J=9.8 Hz, J=2.7 Hz, 1 H) 4.64 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 5.27 - 5.28 (m, 1 H) 7.53 (d, J=8.3 Hz, 2 H) 7.65 (d, J=8.3 Hz, 2 H) 8.99 (d, J=2.9 Hz, 1 H)
509			746 FAB MASS	(300 MHz): 0.80 - 0.83 (m, 6 H) 0.90 (t, J=7.5 Hz, 3 H) 1.07 - 1.30 (m, 16 H) 1.34 (s, 3 H) 1.41 - 1.82 (m, 6 H) 2.02 - 2.54 (m, 22 H) 2.74 - 2.81 (m, 1 H) 2.93 (d, J=14.7 Hz, 1 H) 3.15 - 3.25 (m, 7 H) 3.37 (d, J=8.4 Hz, 1 H) 3.46 - 3.53 (m, 1 H) 3.73 (d, J=8.4 Hz, 1 H) 4.20 (d, J=4.8, 1 H) 4.36 (d, J=7.2 Hz, 1 H) 4.46 (dq, J=9.9 Hz, J=6.0 Hz, 1 H) 4.62 (m, 1 H) 4.90 (d, J=4.2 Hz, 1 H)
510			955	mixture of diastereomers (400 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.91 (t, J=7.32 Hz, 3 H) 1.08 - 1.34 (m, 22 H) 1.49 - 1.91 (m, 5 H) 2.13 - 2.76 (m, 6 H) 2.30 (s, 3 H) 2.37 (s, 6 H) 2.77 - 2.87 (m, 1 H) 2.90 (d, J=14.65 Hz, 1 H) 3.11 -3.49 (m, 12 H) 3.52 - 3.74 (m, 3 H) 3.84 - 3.91 (m, 3 H) 4.15 - 4.25 (m, 1 H) 4.32 - 4.49 (m, 2 H) 4.54 (d, J=9.76 Hz, 1 H) 4.59 - 4.69 (m, 1 H) 4.98 (d, J=4.64 Hz, 1 H) 5.02 - 5.29 (m, 1 H) 6.73 - 6.85 (m, 3 H)

[0877] 

[Table 11-55]

511			955	mixture of diastereomers (400 MHz) : 0.83 (d, J=6.84 Hz, 6 H) 0.91 (t, J=7.33 Hz, 3 H) 1.09 - 1.41 (m, 17 H) 1.12 (d, J=7.73 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.91 (m, 5 H) 2.08 - 2.48 (m, 6 H) 2.30 (s, 3 H) 2.33 (s, 3 H) 2.37 (s, 3 H) 2.57 - 2.93 (m, 5 H) 3.20 -3.49 (m, 6 H) 3.23 (s, 3 H) 3.37 (s, 3 H) 3.50 - 3.64 (m, 1 H) 3.71 (d, J=8.06 Hz, 1 H) 3.79 - 3.88 (m, 1 H) 4.15 - 4.27 (m, 1 H) 4.33 - 4.48 (m, 2 H) 4.51 - 4.57 (m, 1 H) 4.59 - 4.70 (m, 1 H) 4.98 (d, J=4.64 Hz, 1 H) 5.08 - 5.25 (m, 1 H) 6.22 - 6.29 (m, 1 H) 6.56 - 6.64 (m, 1 H)
512			985	mixture of diastereomers (400 MHz) : 0.82 (d, J=6.84 Hz, 6 H) 0.90 (t, J=7.33 Hz, 3 H) 1.08 - 1.32 (m, 17 H) 1.32 (s, 3 H) 1.42 (d, J=6.83 Hz, 3 H) 1.50 - 1.89 (m, 5 H) 2.13 - 2.45 (m, 3 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.54 - 2.64 (m, 1 H) 2.65 -2.87 (m, 3 H) 2.90 (d, J=14.9 Hz, 1 H) 3.17 - 3.59 (m, 10 H) 3.23 (s, 3 H) 3.70 (d, J=6.83 Hz, 1 H) 3.83 (s, 3 H) 3.89 - 3.95 (m, 4 H) 4.18 - 4.27 (m, 1 H) 4.35 - 4.46 (m, 2 H) 4.52 - 4.57 (m, 1 H) 4.60 - 4.68 (m, 1 H) 4.98 (d, J=4.64 Hz, 1 H) 5.09 - 5.17 (m, 1 H) 6.36 (d, J=8.30 Hz, 1 H) 6.65 (d, J=8.55 Hz, 1 H)
513			969	mixture of diastereomers (400 MHz) : 0.83 (d, J=6.83 Hz, 6 H) 0.91 (t, J=7.56Hz, 3 H) 1.08 - 1.34 (m, 23 H) 1.49 - 1.92 (m, 5 H) 2.12 - 2.69 (m, 6 H) 2.30 (s, 3 H) 2.34 (s, 3 H) 2.37 (s, 3 H) 2.77 -2.87 (m, 1 H) 2.90 (d, J=14.9 Hz, 1 H) 3.12 - 3.52 (m, 9 H) 3.24 (s, 3 H) 3.46 (s, 3 H) 3.54 - 3.62 (m, 1 H) 3.66 (q, J=6.59 Hz, 1 H) 3.71 (d, J=8.06 Hz, 1 H) 4.15 - 4.25 (m, 1 H) 4.33 - 4.49 (m, 2 H) 4.54 (d, J=9.76 Hz, 1 H) 4.61 - 4.67 (m, 3 H) 4.98 (d, J=4.64 Hz, 1 H) 5.12 - 5.31 (m, 1 H) 6.77 - 6.84 (m, 1 H) 6.93 - 6.97 (m, 1 H) 7.08 - 7.16 (m, 1 H)
514			955	mixture of diastereomers (400 MHz) : 0.82 (d, J=7.08 Hz, 6 H) 0.91 (t, J=7.32 Hz, 3 H) 1.08 - 1.34 (m, 17 H) 1.32 (s, 3 H) 1.40 - 1.45 (m, 3 H) 1.49 - 1.91 (m, 5 H) 2.12 - 2.46 (m, 3 H) 2.30 (s, 6 H) 2.37 (s, 3 H) 2.53 - 2.74 (m, 2 H) 2.75 -2.87 (m, 2 H) 2.90 (d, J=14.64 Hz, 1 H) 3.18 -3.64 (m, 10 H) 3.23 (s, 3 H) 3.69 -3.73 (m, 1 H) 3.74 (s, 3 H) 3.85 - 3.92 (m, 1 H) 4.16 - 4.27 (m, 1 H) 4.35 - 4.47 (m, 2 H) 4.54 (d, J=9.77 Hz, 1 H) 4.60 - 4.70 (m, 1 H) 4.99 (d, J=4.64 Hz, 1 H) 5.17 (t, J=5.86 Hz, 1 H) 6.51 - 6.54 (m, 1 H) 6.68 - 6.71 (m, 2 H)
515			941.5	mixture of diastereomers (400 MHz) : 0.83 (d, J=7.08 Hz, 6 H) 0.91 (t, J=7.32 Hz, 3 H) 1.08 - 1.30 (m, 17 H) 1.32 (s, 3 H) 1.39 (d, J=6.59 Hz, 3 H) 1.50 - 1.91 (m, 5 H) 2.12 - 2.49 (m, 4 H) 2.31 (s, 3 H) 2.32 (s, 3 H) 2.38 (s, 3 H) 2.58 - 2.67 (m, 1 H) 2.69 -2.87 (m, 3 H) 2.91 (d, J=15.14 Hz, 1 H) 3.19 -3.61 (m, 8 H) 3.23 (s, 3 H) 3.35 (s, 3 H) 3.67 -3.74 (m, 1 H) 4.16 - 4.29 (m, 1 H) 4.32 - 4.51 (m, 1 H) 4.54 (d, J=9.77 Hz, 1 H) 4.59 - 4.69 (m, 1 H) 4.95 - 5.20 (m, 1 H) 6.26 - 6.32 (m, 2 H) 6.90 - 6.96 (m, 1 H)

[0878] 

[Table 11-56]

516			931.6	(400 MHz) : 0.81 (d, J=7.08 Hz, 6 H) 0.90 (t, J=7.32 Hz, 3 H) 1.05 - 1.33 (m, 14 H) 1.13 (s, 3 H) 1.29 (s, 3 H) 1.48 - 1.89 (m, 5 H) 2.08 - 2.55 (m, 6 H) 2.24 (s, 6 H) 2.36 (s, 3 H) 2.76 -2.94 (m, 2 H) 3.14 - 3.51 (m, 6 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.60 -3.71 (m, 3 H) 4.14 - 4.25 (m, 1 H) 4.34 - 4.42 (m, 2 H) 4.61 - 4.70 (m, 1 H) 4.62 (d, J=9.76 Hz, 1 H) 4.91 - 4.97 (m, 1 H) 4.98 (d, J=4.64 Hz, 1 H) 5.36 (t, J=6.35 Hz, 1 H) 6.55 (d, J=7.32 Hz, 1 H) 7.23 (d, J=8.30 Hz, 1 H) 7.33 (t, J=7.81 Hz, 1 H) 7.39 - 7.47 (m, 2 H) 7.75 - 7.82 (m, 2 H)
517			921.5	(400 MHz) : 0.79 - 0.86 (m, 6 H) 0.90 (t, J=7.30 Hz, 3 H) 0.96 - 1.38 (m, 8 H) 1.05 (d, J=6.08 Hz, 3 H) 1.09 (d, J=7.31 Hz, 3 H) 1.16 (s, 3 H) 1.29 (s, 3 H) 1.48 - 1.89 (m, 5 H) 2.12 - 2.51 (m, 4 H) 2.20 (s, 6 H) 2.36 (s, 3 H) 2.60 - 2.95 (m, 8 H) 3.13 (dd, J=2.68, 9.89 Hz, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 -3.53 (m, 4 H) 3.61 (s, 2 H) 3.67 (d, J=8.04 Hz, 1 H) 4.13 - 4.20 (m, 1 H) 4.28 - 4.37 (m, 1 H) 4.39 (d, J=7.07 Hz, 1 H) 4.52 (d, J=9.74 Hz, 1 H) 4.59 - 4.71 (m, 1 H) 4.96 (d, J=4.63 Hz, 1 H) 5.47 (t, J=4.88 Hz, 1 H) 6.98 - 7.02 (m, 1 H) 7.07-7.16 (m, 3 H)
518			760 FAB MASS	(400 MHz) : 0.82 - 0.83 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 1.10 - 1.12 (m, 6 H) 1.17 - 1.32 (m, 13 H) 1.48 - 1.97 (m, 6 H) 2.03 (s, 3 H) 2.14 - 2.54 (m, 15 H) 2.81 (dq, J=7.3 Hz, J=5.1 Hz, 1 H) 2.90 (d, J=14.7 Hz, 1 H) 3.23 - 3.30 (m, 7 H) 3.40 - 3.49 (m, 2 H) 3.64 - 3.74 (m, 2 H) 4.12 (dq, J=10.0 Hz, J=6.3 Hz, 1 H) 4.24 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 5.90 (d, J=9.5 Hz, 1 H)
519			762.4	(400 MHz) : 0.82 - 0.84 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 1.09 (d, J=7.3 Hz, 3 H) 1.16 - 1.32 (m, 16 H) 1.51 - 1.86 (m, 6 H) 2.01 (d, J=9.8 Hz, 1 H) 2.20 - 2.55 (m, 15 H) 2.75 - 2.84 (m, 2 H) 2.89 (d, J=14.4 Hz, 1 H) 3.04 - 3.13 (m, 1 H) 3.20 - 3.25 (m, 4 H) 3.30 (s, 3 H) 3.42 (m, 1 H) 3.52 - 3.59 (m, 2 H) 3.73 (d, J=5.1 Hz, 1 H) 4.06 (dq, J=9.6 Hz, J=6.2 Hz, 1 H) 4.14 (d, J=3.9 Hz, 1 H) 4.42 (d, J=7.1 Hz, 1 H) 4.66 (m, 1 H) 4.95 (d, J=4.6 Hz, 1 H)
520			796.3	(400 MHz) : 0.82 - 0.84 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 1.10 (d, J=7.3 Hz, 3 H) 1.14 - 1.33 (m, 16 H) 1.52 - 1.80 (m, 6 H) 2.19- 2.53 (m, 15 H) 2.81 (dq, J=7.3 Hz, J=5.1 Hz, 1 H) 2.89 (d, J=14.4 Hz, 1 H) 3.02 (s, 3 H) 3.14 (dd, J=9.5 Hz, J=9.3 Hz, 1 H) 3.20 - 3.24 (m, 4 H) 3.30 (s, 3 H) 3.41 - 3.49 (m, 2 H) 3.66 (d, J=8.1 Hz, 1 H) 4.14 - 4.20 (m, 2 H) 4.35 (d, J=7.3 Hz, 1 H) 4.65 (m, 1 H) 4.90 (d, J=9.0 Hz, 1 H) 4.98 (d, J=4.6 Hz, 1 H)
521			966.5	(400 MHz) : 0.81 - 0.83 (m, 6 H) 0.91 (t, J=7.3 Hz, 3 H) 0.97 (m, 3 H) 0.99 - 1.27 (m, 19 H) 1.33 (s, 3 H) 1.52 - 1.92 (m, 6 H) 2.13 - 2.58 (m, 19 H) 2.81 (dq, J=7.2 Hz, J=5.2 Hz, 1 H) 2.89 (d, J=15.4 Hz, 1 H) 3.20 - 3.24 (m, 7 H) 3.30 (s, 3 H) 3.41 - 3.49 (m, 2 H) 3.71 (d, J=8.3 Hz, 1 H) 3.85 (s, 3 H) 4.03 - 4.13 (m, 1 H) 4.23 (m, 1 H) 4.35 - 4.40 (m, 2 H) 4.63 (m, 1 H) 4.71 (m, 1 H) 4.98 (d, J=4.4 Hz, 1 H) 6.88 - 7.00 (m, 2 H) 7.21 - 7.33 (m, 2 H)

[0879] 

[Table 11-57]

522			965.6	(300 MHz) : 0.82 (d, J=6.87 Hz, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.13 (t, J=7.1 Hz, 3 H) 1.06 - 1.35 (m, 17 H) 1.09 (s, 3 H) 1.32 (s, 3 H) 1.48 - 1.94 (m, 4 H) 1.56 (dd, J=4.94, 15.11 Hz, 1 H) 2.10 - 2.74 (m, 12 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.76 - 2.94 (m, 2 H) 3.16 - 3.26 (m, 1 H) 3.22 (s, 3 H) 3.29 (s, 3 H) 3.34 - 3.47 (m, 2 H) 3.64 - 3.76 (m, 2 H) 3.81 (s, 3 H) 4.02 - 4.17 (m, 1 H) 4.20 - 4.28 (m, 1 H) 4.33 - 4.39 (m, 2 H) 4.56 - 4.70 (m, 1 H) 4.98 (d, J=4.40 Hz, 1 H) 5.85 (d, J=9.61 Hz, 1 H) 6.86 (d, J=8.24 Hz, 1 H) 6.94 (t, J=7.15 Hz, 1 H) 7.20 (t, J=7.42 Hz, 1 H) 7.36 - 7.52 (m, 1 H)
523			846.5	(400 MHz) : 0.82 (d, J=6.82 Hz, 6 H) 0.84 - 0.94 (m, 6 H) 1.08 - 1.35 (m, 5 H) 1.10 (d, J=7.07 Hz, 3H) 1.13 (s, 3 H) 1.17 (d, J=7.31 Hz, 3 H) 1.33(s, 3 H) 1.52 - 1.90 (m, 7 H) 1.91 - 2.50 (m, 6 H) 2.26 (s, 6 H) 2.33 (s, 6 H) 2.38 (s, 3 H) 2.53 - 2.63 (m, 1 H) 2.75 -2.86 (m, 1 H) 2.92 (d, J=15.35 Hz, 1 H) 3.21 - 3.33 (m, 4 H) 3.22 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.53 (m, 3 H) 3.69 (d, J=8.08 Hz, 1 H) 4.08 - 4.24 (m, 2 H) 4.36 (d, J=7.31 Hz, 1 H) 4.57 - 4.70 (m, 1 H) 4.92 - 5.02 (m, 1 H) 4.97 (d, J=4.38 Hz, 1 H)
524			951.5	(300 MHz) : 0.81 - 0.92 (m, 9 H) 0.99 - 1.37 (m, 25 H) 1.46 - 2.01 (m, 11 H) 2.20 - 2.57 (m, 19 H) 2.77 - 2.91 (m, 4 H) 3.16 - 3.32 (m, 7 H) 3.40 (m, 1 H) 3.65 - 3.75 (m, 2 H) 3.81 (s, 3 H) 3.97 - 4.11 (m, 2 H) 4.33 - 4.38 (m, 1 H) 4.43 (d, J=7.2 Hz, 1 H) 4.66 (m, 1 H) 4.92 (d, J=4.5 Hz, 1 H) 6.85 (d, J=8.1 Hz, 1 H) 6.94 (m, 1 H) 7.21 (m, 1 H) 7.46 (m, 1 H)
525			832.4	(300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.10 (d, J=7.14 Hz, 3 H) 1.13 (s, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.20 - 1.32(m, 8 H) 1.33 (s, 3 H) 1.49 - 1.63 (m, 2 H) 1.63 - 1.89 (m, 3 H) 1.92- 2.11 (m, 2 H) 2.11 - 2.47 (m, 21 H) 2.48 - 2.59 (m, 1 H) 2.75 - 2.86 (m, 1 H) 2.87 - 2.96 (m, 1 H) 3.18 - 3.34 (m, 8 H) 3.37 - 3.56 (m, 3 H) 3.70 (d, J=7.97 Hz, 1 H) 4.04 - 4.24 (m, 2 H) 4.35 (d, J=7.14 Hz, 1 H) 4.58 - 4.68 (m, 1 H) 4.97 (d, J=4.40 Hz, 1 H) 4.99 - 5.08 (m, 2 H)
526			860.3	(300 MHz) : 0.78 - 0.87 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.10 (d, J=7.14 Hz, 3 H) 1.13 (s, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.19 - 1.30 (m, 8 H) 1.35 (s, 3 H) 1.48 - 1.90 (m, 8 H) 2.02 - 2.46 (m, 21 H) 2.47 - 2.58 (m, 1 H) 2.71 - 2.86 (m, 1 H) 2.88 - 2.98 (m, 1 H) 3.12 - 3.31 (m, 8 H) 3.36 - 3.58 (m, 3 H) 3.69 (d, J=7.97 Hz, 1 H) 4.04 - 4.24 (m, 2 H) 4.33 (d, J=7.42 Hz, 1 H) 4.56 - 4.68 (m, 1 H) 4.88 (d, J=9.62 Hz, 1 H) 4.96 (d, J=4.12 Hz, 1 H) 5.00 - 5.11 (m, 1 H)
527			882.2	(300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.42 Hz, 3 H) 1.08 (d, J=7.14 Hz, 3 H) 1.13 (s, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.19 - 1.30(m, 8 H) 1.37 (s, 3 H) 1.49 - 1.63 (m, 2 H) 1.68 - 1.90 (m, 3 H) 2.10- 2.50 (m, 14 H) 2.54 - 2.66 (m, 1 H) 2.73 - 2.85 (m, 1 H) 2.89 - 3.00 (m, 4 H) 3.18 - 3.59 (m, 13 H) 3.66 (d, J=7.42 Hz, 1 H) 4.07 - 4.20 (m, 2 H) 4.29 (d, J=7.14 Hz, 1 H) 4.57 - 4.68 (m, 1 H) 4.95 (d, J=4.12 Hz, 1 H) 5.27 - 5.40 (m, 1 H) 5.51 - 5.62 (m, 1 H)

[0880] 

[Table 11-58]

528			846.3	(300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.42 Hz, 3 H) 1.09 (d, J=7.14 Hz, 3 H) 1.12 (s, 3 H) 1.14 - 1.30 (m, 11 H) 1.36 (s, 3 H) 1.48 - 1.63 (m, 2 H) 1.67 - 1.89 (m, 3 H) 1.95 (s, 3 H) 2.02 - 2.49 (m, 14 H) 2.49 - 2.62 (m, 1 H) 2.74 - 2.85 (m, 1 H) 2.88 - 2.99 (m, 1 H) 3.16 - 3.57 (m, 13 H) 3.66 (d, J=7.42 Hz, 1 H) 4.07 - 4.21 (m, 2 H) 4.29 (d, J=7.14 Hz, 1 H) 4.57 - 4.68 (m, 1 H) 4.95 (d, J=4.12 Hz, 1 H) 5.19 - 5.32 (m, 1 H) 5.49 - 5.59 (m, 1 H) 6.85 (br s, 1 H)
529			964 FAB MASS	mixture of diastereomers (300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.04 - 1.40 (m, 20 H) 1.47 - 2.05 (m, 6 H) 2.10 - 2.64 (m, 17 H) 2.66 - 3.08 (m, 4 H) 3.12 - 3.32 (m, 8 H) 3.36 - 3.54 (m, 4 H) 3.64 - 3.75 (m, 1 H) 3.77 - 3.89 (m, 4 H) 4.02 - 4.31 (m, 3 H) 4.31 - 4.38 (m, 1 H) 4.57 - 4.69 (m, 1 H) 4.78 - 5.04 (m, 3 H) 6.82 - 6.92 (m, 2 H) 7.15 - 7.24 (m, 1 H) 7.39 - 7.49 (m, 1 H)
530			964.4	mixture of diastereomers (400 MHz) : 0.78 - 0.88 (m, 6 H) 0.91 (t, J=7.31 Hz, 3 H) 1.09 (d, J=7.14 Hz, 3 H) 1.05 - 1.14 (m, 6 H) 1.14- 1.29 (m, 11 H) 1.29 - 1.40 (m, 6 H) 1.50 - 1.65 (m, 2 H) 1.70 - 1.93 (m, 3 H) 2.11 - 2.30 (m, 1 H) 2.20 - 2.56 (m, 18 H) 2.77 - 2.87 (m, 1 H) 2.90 - 2.98 (m, 1 H) 3.10 - 3.38 (m, 14 H) 3.48 - 3.55 (m, 1 H) 3.68 - 3.73 (m, 1 H) 3.83 (s, 3 H) 3.92 - 4.01 (m, 1 H) 4.04 - 4.13 (m, 1 H) 4.17 - 4.26 (m, 1 H) 4.36 - 4.43 (m, 1 H) 4.58 - 4.68 (m, 1 H) 4.98 (d, J=4.62 Hz, 1 H) 5.00 - 5.07 (m, 1 H) 6.88 (d, J=8.04 Hz, 1 H) 6.92 - 6.98 (m, 1 H) 7.19 - 7.26 (m, 1 H) 7.38 - 7.44 (m, 1 H)
531			916.4	mixture of diastereomers (300 MHz) : 0.79 - 0.86 (m, 6 H) 0.90 (t, J=7.42 Hz, 3 H) 1.12 (t, J=7.14 Hz, 3 H) 1.06 - 1.96 (m, 26 H) 1.20 (s, 3 H) 1.31 (s, 3 H) 1.93 (d, J=9.61 Hz, 1 H) 2.13 - 2.67 (m, 12 H) 2.30 (s, 6 H) 2.36 (s, 3 H) 2.70 - 2.88 (m, 3 H) 2.93 (s, 3 H) 3.15 (s, 3 H) 3.17 - 3.25 (m, 1 H) 3.25 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.47 (m, 1 H) 3.60 - 3.78 (m, 3 H) 3.94 - 4.15 (m, 2 H) 4.44 (d, J=7.42 Hz, 1 H) 4.60 - 4.72 (m, 1 H) 4.93 (d, J=4.67Hz, 1 H)
532			951.5	(300 MHz) : 0.76 - 0.86 (m, 6 H) 0.90 (t, J=7.14 Hz, 3 H) 1.04 - 1.24 (m, 17 H) 1.24 - 1.38 (m, 6 H) 1.46 - 1.90 (m, 5 H) 2.10 - 2.50 (m, 21 H) 2.50 - 2.83 (m, 5 H) 2.85 - 2.96 (m, 1 H) 3.14 - 3.26 (m, 4 H) 3.32 - 3.48 (m, 4 H) 3.56 - 3.72 (m, 2 H) 3.81 (s, 3 H) 3.86 - 3.95 (m, 1 H) 4.02 - 4.10 (m, 1 H) 4.46 (d, J=7.14 Hz, 1 H) 4.55 - 4.70 (m, 2 H) 4.83 (d, J=5.22 Hz, 1 H) 6.86 (d, J=8.24 Hz, 1 H) 6.91 - 7.00 (m, 1 H) 7.20 (t, J=7.69 Hz, 1 H) 7.41 (m, J=6.59 Hz, 1 H)

[0881] 

[Table 11-59]

533			951 FAB MASS	mixture of diastereomers (300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.03 - 1.28 (m, 14 H) 1.28 - 1.39 (m, 6 H) 1.46 - 1.92 (m, 5 H) 2.00 - 2.56 (m, 9 H) 2.28 (s, 6 H) 2.38 (s, 3 H) 2.62 - 2.87 (m, 6 H) 2.87 - 2.97 (m, 1 H) 3.10 - 3.28 (m, 4 H) 2.35 (s, 3 H) 3.39 - 3.60 (m, 2 H) 3.62 - 3.71 (m, 1 H) 3.76 - 3.88 (m, 1 H) 3.82 (s, 3 H) 4.06 - 4.14 (m, 1 H) 4.37 - 4.51 (m, 2 H) 4.59 - 4.70 (m, 1 H) 4.83 - 4.91 (m, 1 H) 6.86 (d, J=8.52 Hz, 1 H) 6.92 - 7.00 (m, 1 H) 7.14 - 7.23 (m, 1 H) 7.44 - 7.52 (m, 1 H)
534			967.6	(400 MHz) : 0.81 - 0.83 (m, 6 H) 0.90 (t, J=7.3 Hz, 3 H) 0.94 - 1.03 (m, 3 H) 1.08 - 1.31 (m, 22 H) 1.43 - 1.84 (m, 8 H) 2.13 - 2.91 (m, 21 H) 3.18 - 3.40 (m, 10 H) 3.68 (d, J=8.1 Hz, 1 H) 3.80 (s, 3 H) 4.02 - 4.18 (m, 4 H) 4.33 - 4.40 (m, 2 H) 4.63 (m, 1 H) 4.98 (d, J=4.5 Hz, 1 H) 5.10 (d, J=9.9 Hz, 1 H) 6.84 - 6.94 (m, 2 H) 7.19 (ddd, J=8.4 Hz, J=6.9 Hz, J=1.5 Hz, 1 H) 7.37 (dd, J=7.8 Hz, J=1.5 Hz, 1 H)
535			882.4	(400 MHz) : 0.82 (d, J=7.1 Hz, 3 H) 0.82 (d, J=7.1 Hz, 3 H) 0.90 (t, J=7.4 Hz, 3 H) 1.07 - 1.26 (m, 21 H) 1.31 - 1.35 (m, 7 H) 1.70 - 1.90 (m, 4 H) 2.04 - 2.55 (m, 19 H) 2.82 (t, J=6.8 Hz, 1 H) 2.92 (d, J=15.3 Hz, 1 H) 3.19 (dd, J=10.2, 7.4 Hz, 1 H) 3.23 (s, 3 H) 3.34 (s, 3 H) 3.41 (m, 1 H) 3.55 (m, 1 H) 3.67 (d, J=7.8 Hz, 1 H) 4.04 (q, J=6.7 Hz, 1 H), 4.09 (m, 1 H) 4.42 (d, J=7.3Hz, 1 H) 4.46 (q, J=6.8Hz, 1 H) 4.65 (m, 1 H) 4.86 (d, J=4.9 Hz, 1 H) 6.86 (m, 1 H) 6.94 (m, 1 H) 7.21 (m, 1 H) 7.31 (m, 1 H)
536			868.3	(400 MHz) : 0.82 (d, J=7.0 Hz, 3 H) 0.82 (d, J=7.0 Hz, 3 H) 0.90 (t, J=7.3 Hz, 3 H) 1.08 - 1.38 (m, 28 H) 1.85 - 2.00 (m, 2 H) 2.09 - 2.55 (m, 18 H) 2.63 - 2.89 (m, 4 H) 3.19 (dd, J=10.2, 8.2 Hz, 1 H) 3.21 (s, 3 H) 3.35 (s, 3 H) 3.41 (m, 1 H) 3.51 (m, 1 H) 3.67 (d, J=8.0 Hz, 1 H) 3.69 (d, J=14.4Hz, 1 H) 3.79 (d, J=14.4 Hz, 1 H) 3.81 (s, 3 H) 4.09 (m, 1 H) 4.40 (d, J=7.1Hz, 1 H) 4.45 (q, J=6.6Hz, 1 H) 4.63 (m, 1 H) 4.87 (m, 1 H) 6.86 (m, 1 H) 6.91 (m, 1 H) 7.20 - 7.25 (m, 2 H)
537			838.3	(400 MHz) : 0.81 (d, J=7.0 Hz, 3 H) 0.81 (d, J=7.0 Hz, 3 H) 0.90 (t, J=7.3 Hz, 3 H) 1.08- 1.34 (m, 24 H) 1.60 - 1.80 (m, 3 H) 2.14 - 2.54 (m, 17 H) 2.69 - 2.85 (m, 3 H) 2.91 (m, 1 H) 3.20 (m, 1 H) 3.22 (s, 3 H) 3.35 (s, 3 H) 3.36 - 3.52 (m, 3 H) 3.66 (d, J=7.8 Hz, 1 H) 3.70 (d, J=13.3Hz, 1 H) 3.79 (d, J=13.2 Hz, 1 H) 4.10 (m, 1 H) 4.39 (d, J=7.3 Hz, 1 H) 4.43 (q, J=6.6Hz, 1 H) 4.64 (m, 1 H) 4.89 (m, 1 H) 7.24 - 7.32 (m, 4 H)

[0882] 

[Table 11-60]

538			944.3	(300 MHz) : 0.77 - 0.87 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.10 (d, J=7.42 Hz, 3 H) 1.13 (s, 3 H) 1.13 - 1.27(m, 14 H) 1.29 (d, J=6.59 Hz, 3 H) 1.33 (s, 3 H) 1.47 - 1.69 (m, 2 H) 1.71 - 1.91 (m, 2 H) 1.98 (dd, J=5.23 Hz, J=15.4 Hz, 1 H) 2.10 - 2.35 (m, 10 H) 2.38 (s, 3 H) 2.41 - 2.54 (m, 5 H) 2.56 - 2.64 (m, 1 H) 2.69 (d, J=12.4 Hz, 3 H) 2.77 - 2.98 (m, 3 H) 3.16 - 3.25 (m, 1 H) 3.21 (s, 3 H) 3.31 - 3.54 (m, 3 H) 3.35 (s, 3 H) 3.64 - 3.73 (m, 2 H) 4.10 - 4.19 (m, 1 H) 4.34 - 4.49 (m, 2 H) 4.56 (d, J=6.87 Hz, 1 H) 4.59 - 4.69 (m, 1 H) 4.91 (d, J=4.34 Hz, 1 H) 7.20 - 7.34 (m, 5 H)
539			943.5	(300 MHz) : 0.78 - 0.88 (m, 6 H) 0.92 (t, J=7.14 Hz, 3 H) 1.04 - 1.14 (m, 7 H) 1.13 (s, 3 H) 1.14 - 1.24(m, 7 H) 1.27 (d, J=6.87 Hz, 3 H) 1.32 (s, 3 H) 1.48 - 1.69 (m, 2 H) 1.71 - 1.89 (m, 2 H) 1.95 (dd, J=4.67 Hz, J=15.1 Hz, 1 H) 2.11 - 2.35 (m, 10 H) 2.38 (s, 3 H) 2.42 - 2.64 (m, 4 H) 2.77 - 2.98 (m, 3 H) 3.16 - 3.26 (m, 1 H) 3.21 (s, 3 H) 3.28 - 3.38 (m, 1 H) 3.33 (s, 3 H) 3.39 - 3.56 (m, 2 H) 3.67 (d, J=7.14 Hz, 1 H) 3.80 (dd, J=3.85 Hz, J=11.0 Hz, 1 H) 4.11 - 4.19 (m, 1 H) 4.34 - 4.48 (m, 2 H) 4.60 - 4.70 (m, 1 H) 4.76 (d, J=5.77 Hz, 1 H) 4.90 (d, J=4.67 Hz, 1 H) 7.59 (d, J=8.79 Hz, 2 H) 8.21 (d, J=8.79 Hz, 2 H)
540			898.7	(300 MHz) : 0.76 - 0.88 (m, 6 H) 0.91 (t, J=7.14 Hz, 3 H) 1.05 - 1.26 (m, 14 H) 1.28 (d, J=6.87 Hz, 3 H) 1.33 (s, 3 H) 1.47 - 1.69 (m, 2 H) 1.69 - 1.91 (m, 2 H) 1.96 (dd, J=5.22 Hz, J=15.4 Hz, 1 H) 2.10 - 2.36 (m, 10 H) 2.36 - 2.55 (m, 5 H) 2.61 - 2.72 (m, 2 H) 2.77 - 2.98 (m, 3 H) 3.16 - 3.26 (m, 1 H) 3.21 (s, 3 H) 3.30 - 3.42 (m, 1 H) 3.34 (s, 3 H) 3.42 - 3.54 (m, 2 H) 3.64 - 3.74 (m, 2 H) 4.10 - 4.18 (m, 1 H) 4.34 - 4.48 (m, 2 H) 4.58 - 4.70 (m, 2 H) 4.90 (d, J=4.40 Hz, 1 H) 7.23 - 7.42 (m, 5 H)
541			968.5	(300 MHz) : 0.76 - 0.87 (m, 6 H) 0.92 (t, J=7.42 Hz, 3 H) 1.05 - 1.15 (m, 1 H) 1.11 (d, J=7.42 Hz, 3 H) 1.15 - 1.30 (m, 13 H) 1.33 (s, 3 H) 1.48 - 1.69 (m, 2 H) 1.71 - 1.90 (m, 2 H) 2.10 - 2.34 (m, 11 H) 2.34 - 2.54 (m, 5 H) 2.70 - 2.87 (m, 4 H) 2.87 - 2.98 (m, 2 H) 3.16 - 3.25 (m, 1 H) 3.20 (s, 3 H) 3.33 - 3.55 (m, 2 H) 3.37 (s, 3 H) 3.67 (d, J=7.97 Hz, 3 H) 4.09 - 4.18 (m, 1 H) 4.35 - 4.49 (m, 2 H) 4.59 - 4.70 (m, 1 H) 4.72 (dd, J=3.85 Hz, J=8.24 Hz, 1 H) 4.91 (d, J=4.12 Hz, 1 H) 7.23 - 7.40 (m, 5 H)
542			882.5	(300 MHz) : 0.75 - 0.87 (m, 6 H) 0.92 (t, J=7.42 Hz, 3 H) 0.99 (d, J=6.59 Hz, 3 H) 1.04 - 1.29 (m, 14 H) 1.32 (s, 3 H) 1.48 - 1.67 (m, 2 H) 1.70 - 1.90 (m, 2 H) 2.11 - 2.36 (m, 11 H) 2.36 - 2.51 (m, 5 H) 2.66 - 2.89 (m, 4 H) 2.90 - 3.00 (m, 1 H) 3.14 - 3.24 (m, 2 H) 3.20 (s, 3 H) 3.29 - 3.48 (m, 3 H) 3.34 (s, 3 H) 3.56 - 3.69 (m, 2 H) 4.04 - 4.13 (m, 1 H) 4.26 - 4.38 (m, 2 H) 4.60 - 4.72 (m, 1 H) 4.86 (d, J=3.85 Hz, 1 H) 7.12 - 7.21 (m, 2 H) 7.22 - 7.36 (m, 3 H)

[0883] 

[Table 11-61]

543			925.3	(300 MHz) : 0.75 - 0.86 (m, 6 H) 0.91 (t, J=7.42 Hz, 3 H) 1.00 - 1.29 (m, 17 H) 1.33 (s, 3 H) 1.42 (d, J=6.59 Hz, 3 H) 1.47 - 1.69 (m, 2 H) 1.69 - 2.00 (m, 3 H) 2.08 - 2.52 (m, 15 H) 2.76 - 2.99 (m, 2 H) 3.04 - 3.26 (m, 2 H) 3.21 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.51 (m, 2 H) 3.58 - 3.63 (m, 2 H) 3.87 (s, 3 H) 4.05 - 4.18 (m, 1 H) 4.30 - 4.47 (m, 2 H) 4.55 - 4.60 (m, 1 H) 4.84 - 5.01 (m, 3 H) 5.01 - 5.10 (m, 1 H) 6.83 - 6.96 (m, 2 H) 7.16 - 7.31 (m, 3 H)
544			967.4	(300 MHz): 0.81- 0.83 (m, 6 H) 0.90 (t, J=7.1 Hz, 3 H) 1.02 - 1.34 (m, 25 H) 1.50 - 1.76 (m, 9 H) 2.12 - 2.63 (m, 17 H) 2.80 - 2.94 (m, 2 H) 2.99 - 3.51 (m, 12 H) 3.65 - 3.73 (m, 3 H) 3.82 (s, 3 H) 4.18 (m, 1 H) 4.37 - 4.50 (m, 3 H) 4.62 (m, 1 H) 4.92 (d, J=4.8 Hz, 1 H) 6.84 - 6.94 (m, 2 H) 7.21 (ddd, J=7.8 Hz, J=7.8 Hz, J=1.5 Hz, 1 H) 7.31 (dd, J=7.2 Hz, J=1.5Hz, 1 H) 7.98 (m, 1 H)
545			937.4	(300 MHz) : 0.81 - 0.92 (m, 9 H) 0.98 (t, J=6.9 Hz, 3 H) 1.07 - 1.31 (m, 22 H) 1.46 - 1.92 (m, 9 H) 2.16 - 2.68 (m, 21 H) 2.75 - 2.91 (m, 2 H) 3.14 - 3.32 (m, 7 H) 3.41 (m, 1 H) 3.65 - 3.73 (m, 2 H) 3.80 (s, 3 H) 3.95 - 4.10 (m, 2 H) 4.31 (q, J=6.9 Hz, 1 H) 4.43 (d, J=7.2 Hz, 1 H) 4.65 (m, 1 H) 4.92 (d, J=4.8 Hz, 1 H) 6.84 (d, J=8.0 Hz, 1 H) 6.93 (dd, J=7.8 Hz, J=7.5 Hz, 1 H) 7.19 (ddd, J=8.0Hz, J=7.5 Hz, J=1.5 Hz, 1 H) 7.39 (m, 1 H)
546			910.4	(400 MHz) : 0.80 - 0.85 (m, 6 H) 0.91 (m, 3 H) 1.02 - 1.42 (m, 40 H) 1.70 - 1.90 (m, 4 H) 1.95 - 2.65 (m, 18 H) 2.76 - 2.98 (m, 4 H) 3.20 (dd, J=10.2, 7.8 Hz, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.42 (m, 1 H) 3.64 (m, 1 H) 3.70 (d, J=7.8Hz, 1 H) 3.81 (s, 3 H) 4.04 (m, 1 H) 4.42- 4.49 (m, 1 H) 4.61 - 4.76 (m, 2 H) 6.84 (m, 1 H) 6.94 (m, 1 H) 7.24 (m, 1 H) 7.32 (m, 1 H)

[0884] 

[Table 11-62]

547			882.3	(400 MHz) : 0.82 (d, J=6.9 Hz, 3 H) 0.82 (d, J=6.9 Hz, 3 H) 0.89 (t, J=7.3 Hz, 3 H) 1.07 - 1.39 (m, 26 H) 1.69 - 1.89 (m, 3 H) 2.06 - 2.60 (m, 15 H) 2.65 - 2.87 (m, 8 H) 3.17 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.34 (s, 3 H) 3.38 - 3.56 (m, 2 H) 3.66 (d, J=7.8Hz, 1 H) 3.78 (s, 3 H) 4.09 (m, 1 H) 4.40 (d, J=7.1 Hz, 1 H) 4.43 (q, J=6.5 Hz, 1 H) 4.86 (m, 1 H) 6.82 - 6.90 (m, 2 H) 7.11 - 7.20 (m, 2 H)
548			882.3	(400 MHz) : 0.82 (d, J=6.9 Hz, 3 H) 0.82 (d, J=6.9 Hz, 3 H) 0.91 (t, J=7.3 Hz, 3 H) 1.08 - 1.38 (m, 32 H) 1.70 - 1.90 (m, 3 H) 2.05 (dd, J=15.1, 6.1Hz, 1 H) 2.12 - 2.95 (m, 16 H) 3.16 - 3.25 (m, 4 H) 3.34 (s, 3 H) 3.36 - 3.56 (m, 2 H) 3.82 (s, 3 H) 3.66 (d, J=7.8 Hz, 1 H) 4.08 (m, 1 H) 4.41 (d, J=7.1 Hz, 1 H) 4.45 (q, J=6.9 Hz, 1 H) 4.64 (m, 1 H) 4.86 (m, 1 H) 6.83 (m, 2 H) 7.11 (m, 2 H)
549			852.3	(400 MHz): 0.79 - 0.85 (m, 6 H) 0.91 (t, J=8.3 Hz, 3 H) 1.07 - 1.36 (m, 26 H) 1.70 - 1.88 (m, 2 H) 2.06 - 2.54 (m, 17 H) 2.85 - 2.95 (m, 7 H) 3.16 - 3.26 (m, 4 H) 3.34 (s, 3 H) 3.36 - 3.58 (m, 2 H) 3.66 (d, J=7.5Hz, 1 H) 4.08 (m, 1 H) 4.39 (d, J=7.1 Hz, 1 H) 4.43 (q, J=6.6 Hz, 1 H) 4.85 (m, 1 H) 7.17 - 7.31 (m, 5 H)
550			912	(400 MHz) : 0.79 - 0.84 (m, 6 H) 0.92 (t, J=7.4 Hz, 3 H) 1.02 - 1.25 (m, 17 H) 1.32 (s, 3 H) 1.72 - 1.88 (m, 4 H) 2.10 - 2.50 (m, 16 H) 2.62 - 2.77 (m, 5 H) 2.83 (m, 1 H) 2.94 (m, 1 H) 3.16 - 3.47 (m, 13 H) 3.60 - 3.65 (m, 2 H) 3.78 (s, 3 H) 4.11 (m, 1 H) 4.31 - 4.37 (m, 2 H) 4.66 (m, 1 H) 4.89 (m, 1 H) 6.83 (m, 2 H) 7.09 (m, 2 H)
551			898	mixture of diastereomers (400 MHz) : 0.82 (m, 3 H) 0.82 (m, 3 H) 0.91 (t, J=7.3 Hz, 3 H) 1.08 - 1.35 (m, 20 H) 1.60 - 1.90 (m, 8 H) 2.00 - 2.95 (m, 20 H) 3.18 - 3.60 (m, 12 H) 3.67 (m, 1 H) 3.81 (s, 3 H) 4.14 (m, 1 H) 4.32 - 4.48 (m, 2 H) 4.61- 4.69 (m, 2 H) 4.87-4.97 (m, 1 H) 6.89 (m, 2 H) 7.28 (m, 2 H)

Example 262

[0885] 

(1) By using the compound obtained in Example 126, (1) (1.00 g) as a starting material, a 4"-ketone compound (0.99 g) was obtained in the same manner as that of Example 113, (2).

(2) The compound obtained in (1) mentioned above (305 mg) was dissolved in methanol (9 ml), the solution was added with ammonium acetate (249 mg) and sodium cyanoborohydride (30.4 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 30:1) and silica gel column chromatography (NH-form, toluene:ethyl acetate = 50:1) to obtain an amine compound (43.3 mg) of which steric configuration of the 4"-position was S and a mixture of epimers (35.3 mg).

(3) By using the amine compound (25.1 mg) obtained in (2) mentioned above of which steric configuration of the 4"-position was S as a starting material, the compound shown in Table 11 (16.1 mg) was obtained in the same manner as that of Example 7, (4).

Example 263

[0886] 

(1) The compound obtained in Example 262, (1) (109 mg) was dissolved in ethanol (7.3 ml), the solution was added with Raney nickel slurry (2 ml), and the mixture was stirred at room temperature for 7 hours under a hydrogen atmosphere of 3.5 kgt/cm². The reaction mixture was filtered through Celite, and then the filtrate was added with distilled water and ethyl acetate. The layers were separated, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 60:10:0.2) to obtain a hydroxyl compound (40.1 mg) of which steric configuration of the 4"-position was R.

(2) By using the compound obtained in (1) mentioned above (20.3 mg) as a starting material, the compound shown in Table 11 (14.2 mg) was obtained in the same manner as that of Example 7, (4).

Example 264

[0887] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 72 (54.7 mg) as starting materials, the compound shown in Table 11 (72 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 265

[0888] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 73 (54.7 mg) as starting materials, the compound shown in Table 11 (64 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 266

[0889] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 74 (51.7 mg) as starting materials, the compound shown in Table 11 (50 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 267

[0890] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 75 (55.8 mg) as starting materials, the compound shown in Table 11 (43 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 268

[0891] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 76 (50.8 mg) as starting materials, the compound shown in Table 11 (43 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 269

[0892] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 77 (60.6 mg) as starting materials, the compound shown in Table 11 (82 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 270

[0893] By using the compound obtained in Example 126, (2) (250 mg) and the compound obtained in Reference Example 78 (143.3 mg) as starting materials, the compound shown in Table 11 (235 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 271

[0894] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 79 (60.6 mg) as starting materials, the compound shown in Table 11 (97 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 272

[0895] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 80 (65.3 mg) as starting materials, the compound shown in Table 11 (99 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 273

[0896] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 81 (68.1 mg) as starting materials, the compound shown in Table 11 (126 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 274

[0897] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 82 (48 mg) as starting materials, the compound shown in Table 11 (95 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 275

[0898] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 83 (59.4 mg) as starting materials, the compound shown in Table 11 (113 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 276

[0899] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 84 (59.4 mg) as starting materials, the compound shown in Table 11 (119 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 277

[0900] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 85 (63.5 mg) as starting materials, the compound shown in Table 11 (125 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 278

[0901] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 86 (67.8 mg) as starting materials, the compound shown in Table 11 (130 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 279

[0902] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 87 (68.4 mg) as starting materials, the compound shown in Table 11 (83 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 280

[0903] The compound obtained in Example 270 (100 mg) was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (20 mg), and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1 to 5:1:0.1) to obtain the compound shown in Table 11 (54 mg).

Example 281

[0904] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 88 (75.0 mg) as starting materials, the compound shown in Table 11 (126 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 282

[0905] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 89 (75.0 mg) as starting materials, the compound shown in Table 11 (102 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 283

[0906] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 90 (75.0 mg) as starting materials, the compound shown in Table 11 (104 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 284

[0907] By using the compound obtained in Example 126, (2) (110 mg) and the compound obtained in Reference Example 91 (57.3 mg) as starting materials, the compound shown in Table 11 (77 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 285

[0908] The compound obtained in Example 279 (50 mg) was dissolved in a mixed solvent of isopropanol (4 ml) and distilled water (2 ml), the solution was added with iron (5.4 mg), and the mixture was stirred at 90°C for 1 hour. The reaction mixture was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 11 (32 mg).

Example 286

[0909] The compound obtained in Example 274 (53 mg) was dissolved in chloroform (1 ml), the solution was added with acetaldehyde (13 mg) and sodium triacetoxyborohydride (18 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the compound shown in Table 11 (44.8 mg).

Example 287

[0910] 

(1) The compound obtained in Example 126, (2) (150 mg) was dissolved in tetrahydrofuran (0.2 ml), the solution was added with the compound obtained in Reference Example 92 (55 mg), and the mixture was stirred at room temperature for 3 days. The reaction mixture was added with chloroform and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine =15:10:0.2) to obtain a carbamate compound (169 mg).

(2) By using the compound obtained in (1) mentioned above (169 mg) as a starting material, the compound shown in Table 11 (100 mg) was obtained in the same manner as that of Example 7, (4).

Example 288

[0911] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 93 (70 mg) as starting materials, the compound shown in Table 11 (111 mg) was obtained in the same manners as those of Example 287, (1) and Example 7, (4).

Example 289

[0912] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 94 (70 mg) as starting materials, the compound shown in Table 11 (110 mg) was obtained in the same manners as those of Example 287, (1) and Example 7, (4).

Example 290

[0913] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 95 (48 mg) as starting materials, the compound shown in Table 11 (106 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 291

[0914] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 96 (70 mg) as starting materials, the compound shown in Table 11 (103 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 292

[0915] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 97 (52 mg) as starting materials, the compound shown in Table 11 (107 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 293

[0916] By using the compound obtained in Example 290 (80 mg) as a starting material, the compound shown in Table 11 (65 mg) was obtained in the same manner as that of Example 286.

Example 294

[0917] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 98 (76 mg) as starting materials, the compound shown in Table 11 (50 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 295

[0918] By using the compound obtained in Example 291 (70 mg) as a starting material, the compound shown in Table 11 (70 mg) was obtained in the same manner as that of Example 286.

Example 296

[0919] By using the compound obtained in Example 292 (70 mg) as a starting material, the compound shown in Table 11 (61 mg) was obtained in the same manner as that of Example 286.

Example 297

[0920] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 99 (48 mg) as starting materials, the compound shown in Table 11 (26 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 298

[0921] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 100 (52 mg) as starting materials, the compound shown in Table 11 (117 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 299

[0922] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 101 (80 mg) as starting materials, the compound shown in Table 11 (64 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 300

[0923] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 102 (80 mg) as starting materials, the compound shown in Table 11 (65 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 301

[0924] By using the compound obtained in Example 294 (35 mg) as a starting material, the compound shown in Table 11 (26 mg) was obtained in the same manner as that of Example 286.

Example 302

[0925] By using the compound obtained in Example 297 (17 mg) as a starting material, the compound shown in Table 11 (14 mg) was obtained in the same manner as that of Example 286.

Example 303

[0926] By using the compound obtained in Example 298 (70 mg) as a starting material, the compound shown in Table 11 (67 mg) was obtained in the same manner as that of Example 286.

Example 304

[0927] By using the compound obtained in Example 299 (43 mg) as a starting material, the compound shown in Table 11 (40 mg) was obtained in the same manner as that of Example 286.

Example 305

[0928] By using the compound obtained in Example 300 (65 mg) as a starting material, the compound shown in Table 11 (24 mg) was obtained in the same manner as that of Example 286.

Example 306

[0929] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 103 (51.9 mg) as starting materials, the compound shown in Table 11 (127 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 307

[0930] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 104 (60.3 mg) as starting materials, the compound shown in Table 11 (118 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 308

[0931] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 105 (57.2 mg) as starting materials, the compound shown in Table 11 (120 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 309

[0932] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 106 (51.9 mg) as starting materials, the compound shown in Table 11 (105 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 310

[0933] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 107 (60.0 mg) as starting materials, the compound shown in Table 11 (128 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 311

[0934] By using the compound obtained in Example 307 (65 mg) as a starting material, the compound shown in Table 11 (53 mg) was obtained in the same manner as that of Example 286.

Example 312

[0935] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 108 (60.3 mg) as starting materials, the compound shown in Table 11 (120 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 313

[0936] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 109 (56.0 mg) as starting materials, the compound shown in Table 11 (123 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 314

[0937] By using the compound obtained in Example 306 (65 mg) as a starting material, the compound shown in Table 11 (46 mg) was obtained in the same manner as that of Example 286.

Example 315

[0938] By using the compound obtained in Example 309 (60 mg) as a starting material, the compound shown in Table 11 (63 mg) was obtained in the same manner as that of Example 286.

Example 316

[0939] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 110 (51.9 mg) as starting materials, the compound shown in Table 11 (86 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 317

[0940] By using the compound obtained in Example 311 (35 mg) as a starting material, the compound shown in Table 11 (20 mg) was obtained in the same manner as that of Example 285.

Example 318

[0941] By using the compound obtained in Example 312 (65 mg) as a starting material, the compound shown in Table 11 (73 mg) was obtained in the same manner as that of Example 286.

Example 319

[0942] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 111 (59.7 mg) as starting materials, the compound shown in Table 11 (125 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 320

[0943] By using the compound obtained in Example 308 (60 mg) as a starting material, the compound shown in Table 11 (67 mg) was obtained in the same manner as that of Example 286.

Example 321

[0944] By using the compound obtained in Example 313 (70 mg) as a starting material, the compound shown in Table 11 (72 mg) was obtained in the same manner as that of Example 286.

Example 322

[0945] By using the compound obtained in Example 126, (2) (164 mg) and the compound obtained in Reference Example 112 (103 mg) as starting materials, the compound shown in Table 11 (110 mg) was obtained in the same manners as those of Example 287, (1) and Example 7, (4).

Example 323

[0946] By using the compound obtained in Example 310 (70 mg) as a starting material, the compound shown in Table 11 (66 mg) was obtained in the same manner as that of Example 286.

Example 324

[0947] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 113 (64.0 mg) as starting materials, the compound shown in Table 11 (130 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 325

[0948] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 114 (76 mg) as starting materials, the compound shown in Table 11 (100 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 326

[0949] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 115 (80 mg) as starting materials, the compound shown in Table 11 (106 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 327

[0950] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 116 (69 mg) as starting materials, the compound shown in Table 11 (96 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 328

[0951] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 117 (85 mg) as starting materials, the compound shown in Table 11 (80 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 329

[0952] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 118 (76 mg) as starting materials, the compound shown in Table 11 (101 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 330

[0953] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 119 (89 mg) as starting materials, the compound shown in Table 11 (123 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 331

[0954] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 120 (62 mg) as starting materials, the compound shown in Table 11 (125 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 332

[0955] By using the compound obtained in Example 325 (58 mg) as a starting material, the compound shown in Table 11 (34 mg) was obtained in the same manner as that of Example 286.

Example 333

[0956] By using the compound obtained in Example 326 (73 mg) as a starting material, the compound shown in Table 11 (48 mg) was obtained in the same manner as that of Example 286.

Example 334

[0957] By using the compound obtained in Example 327 (68 mg) as a starting material, the compound shown in Table 11 (62 mg) was obtained in the same manner as that of Example 286.

Example 335

[0958] By using the compound obtained in Example 328 (48 mg) as a starting material, the compound shown in Table 11 (47 mg) was obtained in the same manner as that of Example 286.

Example 336

[0959] By using the compound obtained in Example 329 (60 mg) as a starting material, the compound shown in Table 11 (58 mg) was obtained in the same manner as that of Example 286.

Example 337

[0960] By using the compound obtained in Example 330 (74 mg) as a starting material, the compound shown in Table 11 (67 mg) was obtained in the same manner as that of Example 286.

Example 338

[0961] By using the compound obtained in Example 331 (81 mg) as a starting material, the compound shown in Table 11 (53 mg) was obtained in the same manner as that of Example 286.

Example 339

[0962] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 121 (74.1 mg) as starting materials, the compound shown in Table 11 (75 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 340

[0963] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 122 (74.1 mg) as starting materials, the compound shown in Table 11 (108 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 341

[0964] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 123 (75.9 mg) as starting materials, the compound shown in Table 11 (132 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 342

[0965] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 124 (82.5 mg) as starting materials, the compound shown in Table 11 (125 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 343

[0966] By using the compound obtained in Example 339 (40 mg) as a starting material, the compound shown in Table 11 (41 mg) was obtained in the same manner as that of Example 286.

Example 344

[0967] By using the compound obtained in Example 340 (50 mg) as a starting material, the compound shown in Table 11 (51 mg) was obtained in the same manner as that of Example 286.

Example 345

[0968] By using the compound obtained in Example 341 (75 mg) as a starting material, the compound shown in Table 11 (57 mg) was obtained in the same manner as that of Example 286.

Example 346

[0969] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 125 (81.3 mg) as starting materials, the compound shown in Table 11 (10 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 347

[0970] By using the compound obtained in Example 342 (75 mg) as a starting material, the compound shown in Table 11 (58 mg) was obtained in the same manner as that of Example 286.

Example 348

[0971] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 126 (40 mg) as starting materials, the compound shown in Table 11 (17 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 349

[0972] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 127 (64 mg) as starting materials, the compound shown in Table 11 (15 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 350

[0973] 2',4'-Dihydroxyacetophenone (500 mg) was dissolved in dimethylformamide (10 ml), and the solution was added with imidazole (1.34 g) and t-butyldimethylchlorosilane (1.09 g), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product (1.34 g). This crude product was dissolved in methanol (10 ml), the solution was added with ethylenediamine (634 mg), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added to a suspension of sodium borohydride (200 mg) in tetrahydrofuran (50 ml), then the mixture was added with methanol (6 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1). By using the resulting amine compound (62 mg) and the compound obtained in Example 126, (2) (100 mg) as starting materials, the compound shown in Table 11 (5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 351

[0974] 3',5'-Dihydroxyacetophenone (500 mg) was dissolved in dimethylformamide (10 ml), and the solution was added with imidazole (1.34 g) and t-butyldimethylchlorosilane (1.09 g), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was added with ethyl acetate and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product (1.49 g). A portion of the crude product (250 mg) was dissolved in methanol (2 ml), the solution was added with ethylenediamine (118 mg), and the mixture was stirred at room temperature for 16 hours. This mixture was added to a suspension of sodium borohydride (37 mg) in tetrahydrofuran (10 ml), then the mixture was added with methanol (2 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1). By using the resulting amine compound (58 mg) and the compound obtained in Example 126, (2) (100 mg) as starting materials, the compound shown in Table 11 (5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 352

[0975] By using the compound obtained in Example 126, (2) (70 mg) and the compound obtained in Reference Example 128 (15.7 mg) as starting materials, the compound shown in Table 11 (54 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 353

[0976] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 129 (41.5 mg) as starting materials, the compound shown in Table 11 (142 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 354

[0977] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 130 (112.3 mg) as starting materials, the compound shown in Table 11 (131 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 355

[0978] By using the compound obtained in Example 126, (2) (150 mg) and the compound obtained in Reference Example 131 (38.9 mg) as starting materials, the compound shown in Table 11 (113 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 356

[0979] By using the compound obtained in Example 353 (35 mg) as a starting material, the compound shown in Table 11 (32 mg) was obtained in the same manner as that of Example 286.

Example 357

[0980] By using the compound obtained in Example 126, (2) (100 mg) and the compound obtained in Reference Example 132 (68 mg) as starting materials, the compound shown in Table 11 (87 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 358

[0981] 

(1) By using the compound obtained in Example 263, (1) (100 mg) as a starting material, a 4"-O-imidazolylcarbonyl compound (110 mg) was obtained in the same manner as that of Example 126, (2).

(2) By using the compound obtained in (1) mentioned above (20 mg) and N,N-dimethylethylenediamine (16.9 mg) as starting materials, the compound shown in Table 11 (5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 359

[0982] By using the compound obtained in Example 358, (1) (20 mg) and aminoethanol (11.5 mg) as starting materials, the compound shown in Table 11 (6 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 360

[0983] By using the compound obtained in Example 358, (1) (23 mg) and the compound obtained in Reference Example 57 (10.4 mg) as starting materials, the compound shown in Table 11 (7.4 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 361

[0984] By using the compound obtained in Example 358, (1) (27.2 mg) and the compound obtained in Reference Example 54 (9.8 mg) as starting materials, the compound shown in Table 11 (5.7 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 362

[0985] 

(1) The compound obtained in Example 168, (1) (80 mg) was dissolved in methanol (8 ml), the solution was added with sodium methoxide (0.16 g), and the mixture was stirred for 3 days under reflux by heating. The mixture was further added with sodium methoxide (0.16 g), and the mixture was stirred for 7 days under reflux by heating. The mixture was further added with sodium methoxide (0.16 g), and the mixture was stirred for 2 days under reflux by heating. The reaction mixture was added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a hydroxy compound (14 mg).

(2) By using the compound obtained in (1) mentioned above (14 mg) as a starting material, the compound shown in Table 11 (8 mg) was obtained in the same manner as that of Example 7, (4).

Example 363

[0986] 

(1) The compound obtained in Example 168, (1) (60 mg) was dissolved in ethanol (3 ml), the solution was added with 24% aqueous ammonia (3 ml) and pyridine hydrochloride (6 mg), and the mixture was stirred at 70°C for 15 hours in a sealed tube. The reaction mixture was added with chloroform and brine, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1 to 10:1:0.1) to obtain an amine compound (38 mg).

(2) By using the compound obtained in (1) mentioned above (38 mg) as a starting material, the compound shown in Table 11 (4 mg) was obtained in the same manner as that of Example 7, (4).

Example 364

[0987] By using the compound obtained in Example 168, (1) (60 mg) and 40% aqueous methylamine (3 ml) as starting materials, the compound shown in Table 11 (15 mg) was obtained in the same manners as those of Example 363, (1) and Example 7, (4).

Example 365

[0988] By using the compound obtained in Example 168, (1) (60 mg) and 50% aqueous dimethylamine (3 ml) as starting materials, the compound shown in Table 11 (34 mg) was obtained in the same manners as those of Example 363, (1) and Example 7, (4).

Example 366

[0989] 

(1) The compound obtained in Example 363, (1) (64 mg) was dissolved in dichloromethane (6.6 ml), the solution was added with 1,1'-thiocarbonyldiimidazole (14 mg), and the mixture was stirred at room temperature for 13 hours. The mixture was further added with 1,1'-thiocarbonyldiimidazole (7 mg), and the mixture was stirred at room temperature for 4 hours. The mixture was further added with 1,1'-thiocarbonyldiimidazole (7 mg), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with chloroform and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 22:1:0.1) to obtain a cyclized compound (47 mg).

(2) By using the compound obtained in (1) mentioned above (47 mg) as a starting material, the compound shown in Table 11 (34 mg) was obtained in the same manner as that of Example 7, (4).

Example 367

[0990] 

(1) The compound obtained in Example 168, (1) (350 mg) was dissolved in dimethyl sulfoxide (54 ml), the solution was added with sodium methanethiolate (250 mg), and the mixture was stirred at 70°C for 4 hours. The reaction mixture was added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a hydroxy compound (31 mg).

(2) By using the compound obtained in (1) mentioned above (31 mg) as a starting material, the compound shown in Table 11 (17 mg) was obtained in the same manner as that of Example 7, (4).

Example 368

[0991] 

(1) By using the compound obtained in Example 168, (1) (275 mg) as a starting material, a deprotected compound (210 mg) was obtained in the same manner as that of Example 7, (4).

(2) The compound obtained in (1) mentioned above (30 mg) was dissolved in ethanol (0.5 ml), the solution was added with N-(3-aminopropyl)morpholine (29.6 mg) and pyridine hydrochloride (0.95 mg), and the mixture was stirred at 90°C for 36 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain the compound shown in Table 11 (24 mg).

Example 369

[0992] By using the compound obtained in Example 368, (1) (50 mg) and the compound obtained in Reference Example 106 (62 mg) as starting materials, the compound shown in Table 11 (13 mg) was obtained in the same manner as that of Example 168, (2).

Example 370

[0993] By using the compound obtained in Example 368, (1) (30 mg) and N,N-dimethylethylenediamine (45 µl) as starting materials, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 368, (2).

Example 371

[0994] By using the compound obtained in Example 368, (1) (30 mg) and aminoethanol (24.8 µl) as starting materials, the compound shown in Table 11 (28 mg) was obtained in the same manner as that of Example 368, (2).

Example 372

[0995] By using the compound obtained in Example 368, (1) (30 mg) and n-butylamine (40.6 µl) as starting materials, the compound shown in Table 11 (22 mg) was obtained in the same manner as that of Example 368, (2).

Example 373

[0996] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 131 (37.0 mg) as starting materials, the compound shown in Table 11 (38 mg) was obtained in the same manner as that of Example 168, (2).

Example 374

[0997] The compound obtained in Example 368, (1) (50 mg) was dissolved in ethanol, the solution was added with (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol (73 mg) and pyridine hydrochloride (1.6 mg), and the mixture was heated at 90°C for 48 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 20:1:0.1) to obtain the compound shown in Table 11 (23 mg).

Example 375

[0998] By using the compound obtained in Example 368, (1) (30 mg) and 2-amino-1,3-propanediol (18.7 mg) as starting materials, the compound shown in Table 11 (24 mg) was obtained in the same manner as that of Example 368, (2).

Example 376

[0999] By using the compound obtained in Example 368, (1) (30 mg) and 4-nitrophenethylamine (34.1 mg) as starting materials, the compound shown in Table 11 (9 mg) was obtained in the same manner as that of Example 368, (2).

Example 377

[1000] By using the compound obtained in Example 368, (1) (30 mg) and isoamylamine (24 µl) as starting materials, the compound shown in Table 11 (29 mg) was obtained in the same manner as that of Example 368, (2).

Example 378

[1001] By using the compound obtained in Example 368, (1) (30 mg) and 1-(2-aminoethyl)piperidine (29.2 µl) as starting materials, the compound shown in Table 11 (24 mg) was obtained in the same manner as that of Example 368, (2).

Example 379

[1002] By using the compound obtained in Example 368, (1) (30 mg) and 4-(2-aminoethyl)morpholine (26.9 µl) as starting materials, the compound shown in Table 11 (24 mg) was obtained in the same manner as that of Example 368, (2).

Example 380

[1003] By using the compound obtained in Example 368, (1) (30 mg) and 1-(2-aminoethyl)piperazine (26.9 µl) as starting materials, the compound shown in Table 11 (15 mg) was obtained in the same manner as that of Example 368, (2).

Example 381

[1004] By using the compound obtained in Example 368, (1) (30 mg) and N,N-diethylethylenediamine (23.8 mg) as starting materials, the compound shown in Table 11 (28 mg) was obtained in the same manner as that of Example 368, (2).

Example 382

[1005] By using the compound obtained in Example 368, (1) (30 mg) and N-(2-aminoethyl)pyrrolidine (23.4 mg) as starting materials, the compound shown in Table 11 (21 mg) was obtained in the same manner as that of Example 368, (2).

Example 383

[1006] By using the compound obtained in Example 368, (1) (30 mg) and piperidine (17.5 mg) as starting materials, the compound shown in Table 11 (36 mg) was obtained in the same manner as that of Example 368, (2).

Example 384

[1007] By using the compound obtained in Example 368, (1) (30 mg) and morpholine (17.9 mg) as starting materials, the compound shown in Table 11 (28 mg) was obtained in the same manner as that of Example 368, (2).

Example 385

[1008] By using the compound obtained in Example 368, (1) (30 mg) and (1R,2R)-(-)-2-amino-1-phenyl-1,3-propanediol (34.2 mg) as starting materials, the compound shown in Table 11 (36 mg) was obtained in the same manner as that of Example 368, (2).

Example 386

[1009] By using the compound obtained in Example 368, (1) (30 mg) and N-methylethylenediamine (18 µl) as starting materials, the compound shown in Table 11 (9 mg) was obtained in the same manner as that of Example 368, (2).

Example 387

[1010] By using the compound obtained in Example 368, (1) (30 mg) and N-methylethylenediamine (18 µl) as starting materials, the compound shown in Table 11 (9 mg) was obtained in the same manner as that of Example 368, (2).

Example 388

[1011] By using the compound obtained in Example 368, (1) (30 mg) and 1-methylpiperazine (23 µl) as starting materials, the compound shown in Table 11 (18 mg) was obtained in the same manner as that of Example 368, (2).

Example 389

[1012] By using the compound obtained in Example 368, (1) (30 mg) and piperazine (17.7 mg) as starting materials, the compound shown in Table 11 (22 mg) was obtained in the same manner as that of Example 368, (2).

Example 390

[1013] By using the compound obtained in Example 368, (1) (60 mg) and 3-aminopyrrolidine (36.4 µl) as starting materials, the compound shown in Table 11 (39 mg) was obtained in the same manner as that of Example 368, (2).

Example 391

[1014] By using the compound obtained in Example 368, (1) (30 mg) and N,N-dimethyl-1,3-propanediamine (25.8 µl) as starting materials, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 368, (2).

Example 392

[1015] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 133 (24.2 mg) as starting materials, the compound shown in Table 11 (11 mg) was obtained in the same manner as that of Example 368, (2).

Example 393

[1016] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 133 (24.2 mg) as starting materials, a diastereomer of the compound of Example 392 shown in Table 11 (5 mg) was obtained in the same manner as that of Example 368, (2).

Example 394

[1017] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 134 (20.5 mg) as starting materials, the compound shown in Table 11 (16 mg) was obtained in the same manner as that of Example 368, (2).

Example 395

[1018] By using the compound obtained in Example 368, (1) (10 mg) and 2-amino-1-propanol (5.1 mg) as starting materials, the compound shown in Table 11 (10.7 mg) was obtained in the same manner as that of Example 368, (2).

Example 396

[1019] By using the compound obtained in Example 368, (1) (10 mg) and 3-aminopentane (6.0 mg) as starting materials, the compound shown in Table 11 (10.7 mg) was obtained in the same manner as that of Example 368, (2).

Example 397

[1020] By using the compound obtained in Example 368, (1) (10 mg) and N-isopropylethylenediamine (7.0 mg) as starting materials, the compound shown in Table 11 (9.4 mg) was obtained in the same manner as that of Example 368, (2).

Example 398

[1021] By using the compound obtained in Example 368, (1) (10 mg) and 4-aminotetrahydropyrane (6.9 mg) as starting materials, the compound shown in Table 11 (10.5 mg) was obtained in the same manner as that of Example 368, (2).

Example 399

[1022] By using the compound obtained in Example 368, (1) (30 mg) and (3R)-(+)-3-aminopyrrolidine (17.7 mg) as starting materials, the compound shown in Table 11 (26.1 mg) was obtained in the same manner as that of Example 368, (2).

Example 400

[1023] By using the compound obtained in Example 368, (1) (50 mg) and 1-benzyl-3-aminopyrrolidine (60.3 mg) as starting materials, the compound shown in Table 11 (30.7 mg) was obtained in the same manner as that of Example 368, (2).

Example 401

[1024] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 135 (11 mg) as starting materials, the compound shown in Table 11 (3.2 mg) was obtained in the same manner as that of Example 368, (2).

Example 402

[1025] The compound obtained in Example 400 (15 mg) was dissolved in methanol (300 µl), the solution was added with 20% palladium hydroxide-carbon (7.5 mg), and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 11 (8.4 mg).

Example 403

[1026] By using the compound obtained in Example 368, (1) (50 mg) and the compound obtained in Reference Example 136 (90.1 mg) as starting materials, the compound shown in Table 11 (33.4 mg) was obtained in the same manner as that of Example 368, (2).

Example 404

[1027] By using the compound obtained in Example 403 (15 mg) as a starting material, the compound shown in Table 11 (3.0 mg) was obtained in the same manner as that of Example 402.

Example 405

[1028] 

(1) By using the compound obtained in Example 172, (1) (60 mg) and 24% aqueous ammonia (3 ml) as starting materials, an amine compound (52 mg) was obtained in the same manner as that of Example 363, (1).

(2) By using the compound obtained in (1) mentioned above (52 mg) as a starting material, the compound shown in Table 11 (25 mg) was obtained in the same manner as that of Example 7, (4).

Example 406

[1029] By using the compound obtained in Example 368, (1) (30 mg) and (3S)-(-)-3-aminopyrrolidine (17.7 mg) as starting materials, the compound shown in Table 11 (30.7 mg) was obtained in the same manner as that of Example 368, (2).

Example 407

[1030] 

(1) By using the compound obtained in Example 172, (1) (80 mg) as a starting material, a hydroxy compound (27 mg) was obtained in the same manner as that of Example 362, (1).

(2) By using the compound obtained in (1) mentioned above (32 mg) as a starting material, the compound shown in Table 11 (22 mg) was obtained in the same manner as that of Example 7, (4).

Example 408

[1031] By using the compound obtained in Example 172, (1) (70 mg) as a starting material, the compound shown in Table 11 (8 mg) was obtained in the same manners as those of Example 367, (1) and Example 7, (4).

Example 409

[1032] By using the compound obtained in Example 172, (1) (60 mg) and 40% aqueous methylamine (3 ml) as starting materials, the compound shown in Table 11 (20 mg) was obtained in the same manners as those of Example 363, (1) and Example 7, (4).

Example 410

[1033] By using the compound obtained in Example 172, (1) (60 mg) and 50% aqueous dimethylamine (3 ml) as starting materials, the compound shown in Table 11 (29 mg) was obtained in the same manners as those of Example 363, (1) and Example 7, (4).

Example 411

[1034] By using the compound obtained in Example 405, (1) (43 mg) as a starting material, a cyclized compound (26 mg) was obtained in the same manner as that of Example 366, (1).

(2) By using the compound obtained in (1) mentioned above (32 mg) as a starting material, the compound shown in Table 11 (30 mg) was obtained in the same manner as that of Example 7, (4).

Example 412

[1035] 

(1) By using the compound obtained in Example 172, (1) (2.0 g) as a starting material, a deprotected compound (1.4 g) was obtained in the same manner as that of Example 7, (4).

(2) By using the compound obtained in (1) mentioned above (115 mg) and ethylenediamine (52.6 µl) as starting materials, the compound shown in Table 11 (124 mg) was obtained in the same manner as that of Example 368, (2).

Example 413

[1036] By using the compound obtained in Example 412, (1) (100 mg) and 1,3-diaminopropane (57.1 µl) as starting materials, the compound shown in Table 11 (51 mg) was obtained in the same manner as that of Example 368, (2).

Example 414

[1037] By using the compound obtained in Example 412, (1) (100 mg) and 1,4-diaminobutane (27.5 µl) as starting materials, the compound shown in Table 11 (51 mg) was obtained in the same manner as that of Example 368, (2).

Example 415

[1038] By using the compound obtained in Example 412, (1) (100 mg) and aminoethanol (16.5 µl) as starting materials, the compound shown in Table 11 (82 mg) was obtained in the same manner as that of Example 368, (2).

Example 416

[1039] By using the compound obtained in Example 412, (1) (100 mg) and piperidine (27.1 µl) as starting materials, the compound shown in Table 11 (43 mg) was obtained in the same manner as that of Example 368, (2).

Example 417

[1040] By using the compound obtained in Example 412, (1) (100 mg) and 3-amino-1-propanol (52.3 µl) as starting materials, the compound shown in Table 11 (41 mg) was obtained in the same manner as that of Example 368, (2).

Example 418

[1041] By using the compound obtained in Example 412, (1) (100 mg) and piperazine (58.9 mg) as starting materials, the compound shown in Table 11 (96 mg) was obtained in the same manner as that of Example 368, (2).

Example 419

[1042] By using the compound obtained in Example 412, (1) (100 mg) and N,N-dimethylethylenediamine (75 µl) as starting materials, the compound shown in Table 11 (100 mg) was obtained in the same manner as that of Example 368, (2).

Example 420

[1043] By using the compound obtained in Example 412, (1) (100 mg) and 4-amino-1-butanol (63 µl) as starting materials, the compound shown in Table 11 (86 mg) was obtained in the same manner as that of Example 368, (2).

Example 421

[1044] By using the compound obtained in Example 412, (1) (100 mg) and morpholine (60 µl) as starting materials, the compound shown in Table 11 (47 mg) was obtained in the same manner as that of Example 368, (2).

Example 422

[1045] By using the compound obtained in Example 412, (1) (100 mg) and 2-methoxyethylamine (60 µl) as starting materials, the compound shown in Table 11 (71 mg) was obtained in the same manner as that of Example 368, (2).

Example 423

[1046] By using the compound obtained in Example 412, (1) (100 mg) and 2-(methylamino)ethanol (55 µl) as starting materials, the compound shown in Table 11 (64 mg) was obtained in the same manner as that of Example 368, (2).

Example 424

[1047] By using the compound obtained in Example 412, (1) (100 mg) and n-butylamine (68 µl) as starting materials, the compound shown in Table 11 (66 mg) was obtained in the same manner as that of Example 368, (2).

Example 425

[1048] By using the compound obtained in Example 412, (1) (100 mg) and 3-aminopropionitrile (102 µl) as starting materials, the compound shown in Table 11 (14 mg) was obtained in the same manner as that of Example 368, (2).

Example 426

[1049] By using the compound obtained in Example 412, (1) (60 mg) and benzylamine (45 µl) as starting materials, the compound shown in Table 11 (61 mg) was obtained in the same manner as that of Example 368, (2).

Example 427

[1050] By using the compound obtained in Example 412, (1) (60 mg) and 3-(aminomethyl)pyridine (42 µl) as starting materials, the compound shown in Table 11 (52 mg) was obtained in the same manner as that of Example 368, (2).

Example 428

[1051] By using the compound obtained in Example 412, (1) (60 mg) and imidazole (28.2 mg) as starting materials, the compound shown in Table 11 (57 mg) was obtained in the same manner as that of Example 368, (2).

Example 429

[1052] By using the compound obtained in Example 412, (1) (60 mg) and aniline (37 µl) as starting materials, the compound shown in Table 11 (58 mg) was obtained in the same manner as that of Example 368, (2).

Example 430

[1053] 

(1) By using the compound obtained in Example 172, (1) (100 mg) and benzylamine (75 µl) as starting materials, an amine compound (84 mg) was obtained in the same manner as that of Example 368, (2).

(2) The compound obtained in (1) mentioned above (84 mg) was dissolved in methanol (200 µl), the solution was added with 20% palladium hydroxide-carbon (42 mg), and the mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue (72 mg) was dissolved in chloroform (200 µl), the solution was added with pyridine (162 µl) and triphosgene (59.4 mg), and the mixture was stirred for 1 hour under ice cooling. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a cyclized compound (12 mg).

(3) By using the compound obtained in (2) mentioned above (12 mg) as a starting material, the compound shown in Table 11 (10 mg) was obtained in the same manner as that of Example 7, (4).

Example 431

[1054] By using the compound obtained in Example 172, (1) (40 mg) and the compound obtained in Reference Example 54 (15.3 mg) as starting materials, the compound shown in Table 11 (2.4 mg) was obtained in the same manners as those of Example 168, (2) and Example 7, (4).

Example 432

[1055] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 106 (62 mg) as starting materials, the compound shown in Table 11 (18 mg) was obtained in the same manner as that of Example 168, (2).

Example 433

[1056] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 131 (37.0 mg) as starting materials, the compound shown in Table 11 (17 mg) was obtained in the same manner as that of Example 168, (2).

Example 434

[1057] By using the compound obtained in Example 412, (1) (50 mg) and D-(-)-threo-2-amino-1-(4-nitrophenyl)-1,3-propanediol (72.6 mg) as starting materials, the compound shown in Table 11 (37 mg) was obtained in the same manner as that of Example 368, (2).

Example 435

[1058] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 137 (102 mg) as starting materials, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 368, (2).

Example 436

[1059] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 138 (107 mg) as starting materials, the compound shown in Table 11 (39 mg) was obtained in the same manner as that of Example 368, (2).

Example 437

[1060] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 139 (87 mg) as starting materials, the compound shown in Table 11 (36 mg) was obtained in the same manner as that of Example 368, (2).

Example 438

[1061] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 140 (92 mg) as starting materials, the compound shown in Table 11 (52 mg) was obtained in the same manner as that of Example 368, (2).

Example 439

[1062] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 141 (97 mg) as starting materials, the compound shown in Table 11 (51 mg) was obtained in the same manner as that of Example 368, (2).

Example 440

[1063] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 142 (84 mg) as starting materials, the compound shown in Table 11 (15 mg) was obtained in the same manner as that of Example 368, (2).

Example 441

[1064] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 150 (89 mg) as starting materials, the compound shown in Table 11 (21 mg) was obtained in the same manner as that of Example 368, (2).

Example 442

[1065] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 69 (36.0 mg) as starting materials, the compound shown in Table 11 (37 mg) was obtained in the same manner as that of Example 368, (2).

Example 443

[1066] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 68 (47.3 mg) as starting materials, the compound shown in Table 11 (37 mg) was obtained in the same manner as that of Example 368, (2).

Example 444

[1067] By using the compound obtained in Example 412, (1) (50 mg) and N,N-dimethylpropane-1,4-diamine (34.9 mg) as starting materials, the compound shown in Table 11 (37 mg) was obtained in the same manner as that of Example 368, (2).

Example 445

[1068] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 67 (39.7 mg) as starting materials, the compound shown in Table 11 (12.5 mg) was obtained in the same manner as that of Example 368, (2).

Example 446

[1069] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 147 (67.1 mg) as starting materials, the compound shown in Table 11 (31 mg) was obtained in the same manner as that of Example 168, (2).

Example 447

[1070] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 148 (76.7 mg) as starting materials, the compound shown in Table 11 (32 mg) was obtained in the same manner as that of Example 168, (2).

Example 448

[1071] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 145 (121 mg) as starting materials, the compound shown in Table 11 (32 mg) was obtained in the same manner as that of Example 168, (2).

Example 449

[1072] By using the compound obtained in Example 412, (1) (30 mg) and 2-amino-1,3-propanediol (18.7 mg) as starting materials, the compound shown in Table 11 (36 mg) was obtained in the same manner as that of Example 368, (2).

Example 450

[1073] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 143 (37.4 mg) as starting materials, the compound shown in Table 11 (34 mg) was obtained in the same manner as that of Example 368, (2).

Example 451

[1074] 

(1) Florfenicolamine hydrochloride (20 mg) was added with 1 N aqueous sodium hydroxide and chloroform, the layers were separated, the aqueous layer was added with potassium carbonate, and the mixture was extracted with chloroform. The organic layer was concentrated under reduced pressure to obtain an amine compound (17 mg).

(2) By using the compound obtained in Example 412, (1) (12.6 mg) and the compound obtained in (1) mentioned above (17 mg) as starting materials, the compound shown in Table 11 (1.0 mg) was obtained in the same manner as that of Example 368, (2).

Example 452

[1075] By using the compound obtained in Example 412, (1) (30 mg) and (1R,2R)-(-)-2-amino-1-phenyl-1,3-propanediol (34.3 mg) as starting materials, the compound shown in Table 11 (30 mg) was obtained in the same manner as that of Example 368, (2).

Example 453

[1076] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 133 (24.2 mg) as starting materials, the compound shown in Table 11 (8 mg) was obtained in the same manner as that of Example 368, (2).

Example 454

[1077] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 133 (24.2 mg) as starting materials, a diastereomer of the compound of Example 453 shown in Table 11 (10 mg) was obtained in the same manner as that of Example 368, (2).

Example 455

[1078] By using the compound obtained in Example 412, (1) (50 mg) and the compound obtained in Reference Example 144 (39.7 mg) as starting materials, the compound shown in Table 11 (12.5 mg) was obtained in the same manner as that of Example 368, (2).

Example 456

[1079] By using the compound obtained in Example 412, (1) (30 mg) and D-(+)-threo-[1-(p-methanesulfonyl)phenyl]-2-amino-1,3-propanediol (13 mg) as starting materials, the compound shown in Table 11 (12.5 mg) was obtained in the same manner as that of Example 368, (2).

Example 457

[1080] By using the compound obtained in Example 412, (1) (30 mg) and 4-nitrophenethylamine hydrochloride (41.6 mg) as starting materials, the compound shown in Table 11 (13 mg) was obtained in the same manner as that of Example 368, (2).

Example 458

[1081] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 144 (40.2 mg) as starting materials, the compound shown in Table 11 (4.0 mg) was obtained in the same manner as that of Example 368, (2).

Example 459

[1082] 

(1) The amine compound (50 mg) obtained in Example 262, (2) of which steric configuration of the 4"-position was S was dissolved in dimethylformamide (2 ml), the solution was added with N,N'-carbonyldiimidazole (25.7 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (2 ml). The solution was added with the compound obtained in Reference Example 145 (55.9 mg), and the mixture was stirred for 1 hour under reflux by heating. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a urea compound (71 mg).

(2) By using the compound obtained in (1) mentioned above (65 mg) as a starting material, the compound shown in Table 11 (48 mg) was obtained in the same manner as that of Example 7, (4).

Example 460

[1083] 

(1) The compound obtained in Reference Example 146 (20 mg) was dissolved in chloroform, the solution was added with the Dess-Martin reagent (40 mg), and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and diethyl ether, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, the resulting aldehyde and the amine compound (50 mg) obtained in Example 262, (2) of which steric configuration of the 4"-position was S were dissolved in chloroform, the solution was added with sodium triacetoxyborohydride (1.38 g), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain an adduct compound (30 mg).

(2) By using the compound obtained in (1) mentioned above (30 mg) as a starting material, the compound shown in Table 11 (9.5 mg) was obtained in the same manner as that of Example 7, (4).

Example 461

[1084] 

(1) The amine compound (420 mg) obtained in Example 262, (2) of which steric configuration of the 4"-position was S was dissolved in dimethylformamide (8 ml), the solution was added with N,N'-carbonyldiimidazole (180 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a 4"-N-imidazolylcarbonyl compound (462 mg).

(2) The compound obtained in (1) mentioned above (66 mg) was dissolved in tetrahydrofuran (2 ml), the solution was added with the compound obtained in Reference Example 142 (47 mg), and the mixture was stirred for 1 hour under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain a urea compound (72.2 mg).

(3) By using the compound obtained in (2) mentioned above (71.2 mg) as a starting material, the compound shown in Table 11 (16.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 462

[1085] By using the compound obtained in Example 461, (1) (66 mg) and the compound obtained in Reference Example 147 (38 mg) as starting materials, the compound shown in Table 11 (30.4 mg) was obtained in the same manners as those of Example 461, (2) and Example 7, (4).

Example 463

[1086] By using the compound obtained in Example 461, (1) (66 mg) and the compound obtained in Reference Example 148 (48 mg) as starting materials, the compound shown in Table 11 (41.3 mg) was obtained in the same manners as those of Example 461, (2) and Example 7, (4).

Example 464

[1087] 

(1) By using the compound obtained in Example 461, (1) (130 mg) and the compound obtained in Reference Example 137 (44.6 mg) as starting materials, a urea compound (111 mg) was obtained in the same manner as that of Example 126, (3).

(2) By using the compound obtained in (1) mentioned above (50 mg) as a starting material, the compound shown in Table 11 (42 mg) was obtained in the same manner as that of Example 7, (4).

Example 465

[1088] 

(1) By using the compound obtained in Example 461, (1) (60 mg) and the compound obtained in Reference Example 138 (15 mg) as starting materials, a urea compound (23 mg) was obtained in the same manner as that of Example 126, (3).

(2) By using the compound obtained in (1) mentioned above (20 mg) as a starting material, the compound shown in Table 11 (14 mg) was obtained in the same manner as that of Example 7, (4).

Example 466

[1089] 

(1) By using the compound obtained in Example 461, (1) (70 mg) and the compound obtained in Reference Example 149 (17.2 mg) as starting materials, a urea compound (54 mg) was obtained in the same manner as that of Example 126, (3).

(2) By using the compound obtained in (1) mentioned above (50 mg) as a starting material, the compound shown in Table 11 (33 mg) was obtained in the same manner as that of Example 7, (4).

Example 467

[1090] 

(1) The amine compound obtained in Example 262, (2) (70 mg) of which steric configuration of the 4"-position was S was dissolved in dimethylformamide (1.5 ml), the solution was added with N,N'-carbonyldiimidazole (30.0 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (2 ml). The solution was added with the compound obtained in Reference Example 150 (38.5 mg), and the mixture was stirred for 1 hour under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain a urea compound (66.9 mg).

(2) By using the compound obtained in (1) mentioned above (64.3 mg) as a starting material, the compound shown in Table 11 (32.7 mg) was obtained in the same manner as that of Example 7, (4).

Example 468

[1091] By using the amine compound obtained in Example 262, (2) (50 mg) of which steric configuration of the 4"-position was S and n-butylamine (11.6 mg) as starting materials, the compound shown in Table 11 (40 mg) was obtained in the same manners as those of Example 459, (1) and Example 7, (4).

Example 469

[1092] 

(1) The amine compound obtained in Example 262, (2) (50 mg) of which steric configuration of the 4"-position was S was dissolved in chloroform (2 ml), the solution was added with the compound obtained in Reference Example 151 (37.8 mg) and sodium triacetoxyborohydride (16.8 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 50:10:0.2) to obtain an amine compound (37 mg).

(2) By using the compound obtained in (1) mentioned above (35 mg) as a starting material, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 7, (4).

Example 470

[1093] 

(1) The amine compound obtained in Example 262, (2) (60 mg) of which steric configuration of the 4"-position was S was dissolved in chloroform, the solution was added with triethylamine (64 mg) and 3-chloropropanesulfonyl chloride (32 mg), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 10:10:0.2) to obtain a chloro compound (60 mg).

(2) The compound obtained in (1) mentioned above (46 mg) and (1S)-1-(2-methoxyphenyl)ethanamine (19 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) were dissolved in dimethylformamide (0.5 ml), and the solution was heated at 110°C for 5 hours.
The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain an adduct compound (26 mg).

(3) By using the compound obtained in (2) mentioned above (26 mg) as a starting material, the compound shown in Table 11 (9 mg) was obtained in the same manner as that of Example 7, (4).

Example 471

[1094] 

(1) The epimer mixture (48 mg) obtained in Example 262, (2) was dissolved in dichloromethane (0.5 ml), the solution was added with 9-fluorenylmethylsuccinimidyl carbonate (25 mg) and triethylamine (33 µl), and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:ethyl acetate:methanol:28% aqueous ammonia = 50:10:1:1) to obtain a protected amine compound (8.0 mg) of which steric configuration of the 4"-position was R.

(2) The compound obtained in (1) mentioned above (12.2 mg) was dissolved in piperidine (0.3 ml), and the solution was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol = 10:1) to obtain an amine compound (9.2 mg) of which steric configuration of the 4"-position was R.

(3) By using the compound obtained in (2) mentioned above (9.2 mg) as a starting material, the compound shown in Table 11 (4.9 mg) was obtained in the same manner as that of Example 7, (4).

Example 472

[1095] By using the compound obtained in Example 126, (2) (79 mg) and the compound obtained in Reference Example 163 (47.2 mg) as starting materials, the compound shown in Table 11 (25.5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 473

[1096] By using the compound obtained in Example 126, (2) (80.5 mg) and the compound obtained in Reference Example 164 (53.2 mg) as starting materials, the compound shown in Table 11 (23.1 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 474

[1097] By using the compound obtained in Example 126, (2) (79.3 mg) and the compound obtained in Reference Example 165 (41.2 mg) as starting materials, the compound shown in Table 11 (21.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 475

[1098] By using the compound obtained in Example 126, (2) (80.5 mg) and the compound obtained in Reference Example 166 (37.2 mg) as starting materials, the compound shown in Table 11 (22.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 476

[1099] By using the compound obtained in Example 126, (2) (78.3 mg) and the compound obtained in Reference Example 167 (28.7 mg) as starting materials, the compound shown in Table 11 (24.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 477

[1100] By using the compound obtained in Example 126, (2) (81.1 mg) and the compound obtained in Reference Example 168 (42.3 mg) as starting materials, the compound shown in Table 11 (15.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 478

[1101] By using the compound obtained in Example 126, (2) (81.3 mg) and the compound obtained in Reference Example 169 (33.5 mg) as starting materials, the compound shown in Table 11 (16.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 479

[1102] By using the compound obtained in Example 126, (2) (86.7 mg) and the compound obtained in Reference Example 170 (28.4 mg) as starting materials, the compound shown in Table 11 (12.4 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 480

[1103] By using the compound obtained in Example 126, (2) (79.6 mg) and the compound obtained in Reference Example 171 (30.3 mg) as starting materials, the compound shown in Table 11 (17.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 481

[1104] By using the compound obtained in Example 126, (2) (79.9 mg) and the compound obtained in Reference Example 172 (27.5 mg) as starting materials, the compound shown in Table 11 (20.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 482

[1105] 

(1) The compound obtained in Example 126, (2) (80 mg) was dissolved in tetrahydrofuran (0.2 ml), the solution was added with 1,4-butanediamine (77 µl), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and then the organic layer was filtered by using a phase separator. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 5:1:0.1) to obtain a carbamate compound (52.1 mg).

(2) By using the compound obtained in (1) mentioned above (52.1 mg) as a starting material, the compound shown in Table 11 (2.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 483

[1106] By using the compound obtained in Example 126, (2) (80 mg) and 2-aminoethanol (9 µl) as starting materials, the compound shown in Table 11 (10.9 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 484

[1107] By using the compound obtained in Example 126, (2) (80 mg) and 2-methoxyethylamine (13 µl) as starting materials, the compound shown in Table 11 (20.0 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 485

[1108] By using the compound obtained in Example 126, (2) (80 mg) and 2-(N-methylamino)ethanol (12 µl) as starting materials, the compound shown in Table 11 (21.9 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 486

[1109] By using the compound obtained in Example 126, (2) (80 mg) and piperidine (15 µl) as starting materials, the compound shown in Table 11 (36.2 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 487

[1110] By using the compound obtained in Example 126, (2) (80 mg) and morpholine (13 µl) as starting materials, the compound shown in Table 11 (13.3 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 488

[1111] By using the compound obtained in Example 126, (2) (80 mg) and n-butylamine (15 µl) as starting materials, the compound shown in Table 11 (33.5 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 489

[1112] By using the compound obtained in Example 126, (2) (80 mg), methylamine hydrochloride (52 mg) and triethylamine (107 µl) as starting materials, the compound shown in Table 11 (17.0 mg) was obtained in the same manners as those of Example 482, (1) and Example 7, (4).

Example 490

[1113] By using the compound obtained in Example 126, (2) (80 mg) and ethylenediamine (51.3 µl) as starting materials, the compound shown in Table 11 (22.5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 491

[1114] By using the compound obtained in Example 126, (2) (80 mg) and 1,3-propanediamine (64 µl) as starting materials, the compound shown in Table 11 (26.6 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 492

[1115] By using the compound obtained in Example 126, (2) (80 mg) and N,N-dimethylethylenediamine (15.4 µl) as starting materials, the compound shown in Table 11 (28.9 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 493

[1116] By using the compound obtained in Example 126, (2) (80 mg) and 3-aminopropanenitrile (11.3 µl) as starting materials, the compound shown in Table 11 (33.5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 494

[1117] By using the compound obtained in Example 126, (2) (80 mg) and 3-amino-1-propanol (11.7 µl) as starting materials, the compound shown in Table 11 (26.7 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 495

[1118] By using the compound obtained in Example 126, (2) (80 mg) and 4-amino-1-butanol (14.3 µl) as starting materials, the compound shown in Table 11 (21.7 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 496

[1119] By using the compound obtained in Example 126, (2) (80 mg) and 28% aqueous ammonia (46.7 µl) as starting materials, the compound shown in Table 11 (22.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 497

[1120] By using the compound obtained in Example 126, (2) (80 mg) and 50% aqueous dimethylamine (69 µl) as starting materials, the compound shown in Table 11 (31.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 498

[1121] By using the compound obtained in Example 126, (2) (80 mg) and piperazine (132 mg) as starting materials, the compound shown in Table 11 (35.1 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 499

[1122] 

(1) The compound obtained in Example 126, (2) (80 mg) was dissolved in tetrahydrofuran (0.2 ml), the solution was added with the compound obtained in Reference Example 173 (48 mg), and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=15:1:0.1) to obtain a carbamate compound (58.2 mg).

(2) By using the compound obtained in (1) mentioned above (58.2 mg) as a starting material, the compound shown in Table 11 (39.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 500

[1123] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 174 (40 mg) as starting materials, the compound shown in Table 11 (44.0 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 501

[1124] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 175 (51 mg) as starting materials, the compound shown in Table 11 (39.0 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 502

[1125] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 176 (42 mg) as starting materials, the compound shown in Table 11 (43.5 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 503

[1126] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 177 (52 mg) as starting materials, the compound shown in Table 11 (50.8 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 504

[1127] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 178 (51 mg) as starting materials, the compound shown in Table 11 (42.2 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 505

[1128] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 179 (54 mg) as starting materials, the compound shown in Table 11 (50.8 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 506

[1129] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 180 (45 mg) as starting materials, the compound shown in Table 11 (38.8 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 507

[1130] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 181 (45 mg) as starting materials, the compound shown in Table 11 (40.8 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4).

Example 508

[1131] By using the compound obtained in Example 126, (2) (80 mg) and the compound obtained in Reference Example 182 (36 mg) as starting materials, the compound shown in Table 11 (10.0 mg) was obtained in the same manners as those of Example 499, (1) and Example 7, (4) except that dimethylformamide was used instead of tetrahydrofuran.

Example 509

[1132] The compound obtained in Example 262 (11.0 mg) was dissolved in chloroform, the solution was added with 36% aqueous formaldehyde (12.7 µl) and sodium triacetoxyborohydride (4.9 mg), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, potassium carbonate and dichloromethane, the layers were separated, and then the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 5:1:0.1) to obtain the compound shown in Table 11 (6.2 mg).

Example 510

[1133] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 183 (77.0 mg) as starting materials, the compound shown in Table 11 (44.6 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 511

[1134] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 184 (100 mg) as starting materials, the compound shown in Table 11 (44.3 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 512

[1135] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 185 (23.5 mg) as starting materials, the compound shown in Table 11 (19.0 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 513

[1136] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 186 (60.0 mg) as starting materials, the compound shown in Table 11 (47.2 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 514

[1137] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 187 (35.0 mg) as starting materials, the compound shown in Table 11 (55.9 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 515

[1138] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 188 (87.7 mg) as starting materials, the compound shown in Table 11 (14.8 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 516

[1139] 

(1) N-(Naphthalen-1-yl)ethane-1,2-diamine hydrochloride (100 mg) was dissolved in distilled water (5 ml), the solution was added with potassium carbonate and thereby made basic, and then the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain a desalted compound (40 mg).

(2) By using the compound obtained in Example 126, (2) (80.0 mg) and the desalted compound (40 mg) obtained in (1) mentioned above as starting materials, the compound shown in Table 11 (47.8 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 517

[1140] By using the compound obtained in Example 126, (2) (80.0 mg) and the compound obtained in Reference Example 189 (50.0 mg) as starting materials, the compound shown in Table 11 (41.2 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 518

[1141] 

(1) The amine compound (50 mg) obtained in Example 262, (2) of which steric configuration of the 4"-position was S was dissolved in dichloromethane (1 ml), the solution was added with acetic anhydride (6.0 µl) and pyridine (6.4 µl) under ice cooling, and the mixture was stirred for 1.5 hours under ice cooling. The reaction mixture was added with saturated brine and ethyl acetate, the layers were separated, and then the organic layer was dried over anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain an acetyl compound (40.6 mg).

(2) By using the compound obtained in (1) mentioned above (40.6 mg) as a starting material, the compound shown in Table 11 (27.3 mg) was obtained in the same manner as that of Example 7, (4).

Example 519

[1142] 

(1) The amine compound (30 mg) obtained in Example 262, (2) of which steric configuration of the 4"-position was S was dissolved in chloroform (0.6 ml), the solution was added with 2-(t-butyldimethylsilyloxy)acetaldehyde (7.4 µml), sodium triacetoxyborohydride (10.1 mg) and acetic acid (1.8 µl), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 40:10:0.2) to obtain an alkylamine compound (23.1 mg).

(2) By using the compound obtained in (1) mentioned above (23.1 mg) as a starting material, the compound shown in Table 11 (11.9 mg) was obtained in the same manner as that of Example 7, (4).

Example 520

[1143] 

(1) The amine compound obtained in Example 262, (2) (50 mg) of which steric configuration of the 4"-position was S was dissolved in dichloromethane (1 ml), the solution was added with methanesulfonyl chloride (6.1 µl) and triethylamine (14.7 µl) under ice cooling, and the mixture was stirred for 3 hours under ice cooling, and further stirred at room temperature for 4 hours. The reaction mixture was added with saturated brine and ethyl acetate, the layers were separated, and then the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a sulfonamide compound (31.5 mg).

(2) By using the compound obtained in (1) mentioned above (31.5 mg) as a starting material, the compound shown in Table 11 (17.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 521

[1144] 

(1) The amine compound obtained in Example 262, (2) (40 mg) of which steric configuration of the 4"-position was S was dissolved in tetrahydrofuran (0.4 ml), the solution was added with N,N'-carbonyldiimidazole (41.2 mg), and the mixture was stirred overnight at room temperature, and then further stirred at 40°C for 3 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and then the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain an imidazolamide compound (17.3 mg).

(2) The compound obtained in (1) mentioned above (17.3 mg) was dissolved in tetrahydrofuran (0.1 ml), the solution was added with (1S)-1-(2-methoxyphenyl)ethanamine (7.4 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a urea compound (8.7 mg).

(3) By using the compound obtained in (2) mentioned above (11.0 mg) as a starting material, the compound shown in Table 11 (7.5 mg) was obtained in the same manner as that of Example 7, (4).

Example 522

[1145] 

(1) The amine compound obtained in Example 262, (2) (38 mg) of which steric configuration of the 4"-position was S and the compound obtained in Reference Example 191 (33.9 mg) were dissolved in dichloromethane (760 µl), the solution was successively added with 4-dimethylaminopyridine (16.6 mg) and dicyclohexylcarbodiimide (16.6 mg), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form, chloroform) to obtain an amide compound (44.7 mg).

(2) The compound obtained in (1) mentioned above (44.7 mg) was dissolved in dimethylformamide (894 µl), the solution was successively added with benzenethiol (16.9 µl) and potassium carbonate (22.9 mg), and the mixture was stirred at 60°C for 30 minutes. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol = 10:1) to obtain a denitrobenzenesulfonylated compound (20.1 mg).

(3) By using the compound obtained in (2) mentioned above (20.1 mg) and acetaldehyde (4.87 µl) as starting materials, the compound shown in Table 11 (9.8 mg) was obtained in the same manners as those of Example 7, (2) and Example 7, (4).

Example 523

[1146] The amine compound obtained in Example 262, (2) (15.5 mg) of which steric configuration of the 4"-position was S was dissolved in dimethylformamide (100 µl), the solution was added with carbonyldiimidazole (3.02 mg), the mixture was stirred at room temperature for 1 hour, and then added with N,N-dimethylpropane-1,3-diamine (6 µl), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 11 (13.2 mg).

Example 524

[1147] 

(1) The amine compound obtained in Example 262, (2) (60 mg) of which steric configuration of the 4"-position was S was dissolved in chloroform (1.2 ml), the solution was added with the compound obtained in Reference Example 190 (30.9 mg), sodium triacetoxyborohydride (20.2 mg) and acetic acid (3.6 µl), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 50:1:0.1) to obtain an alkylamine compound (68.4 mg).

(2) By using the compound obtained in (1) mentioned above (40 mg) as a starting material, a denitrobenzenesulfonylated compound (20.0 mg) was obtained in the same manner as that of Example 522, (2).

(3) The compound obtained in (2) mentioned above (20.0 mg) was dissolved in chloroform (0.6 ml), the solution was added with acetaldehyde (1.18 µl) and sodium triacetoxyborohydride (5.5 mg) under ice cooling, and the mixture was stirred for 2 hours under ice cooling, and then at room temperature for 1.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and chloroform, the layers were separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 60:10:0.2) to obtain a mono-N-ethyl compound (14.0 mg).

(4) By using the compound obtained in (3) mentioned above (14.0 mg) as a starting material, the compound shown in Table 11 (7.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 525

[1148] By using the compound obtained in Example 461, (1) (20 mg) and N,N-dimethylethylenediamine (7.7 µl) as starting materials, the compound shown in Table 11 (10 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 526

[1149] By using the compound obtained in Example 461, (1) (20 mg) and the compound obtained in Reference Example 67 (12 mg) as starting materials, the compound shown in Table 11 (11 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 527

[1150] By using the compound obtained in Example 461, (1) (20 mg) and the compound obtained in Reference Example 68 (20 mg) as starting materials, the compound shown in Table 11 (15 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 528

[1151] By using the compound obtained in Example 461, (1) (20 mg) and the compound obtained in Reference Example 69 (15 mg) as starting materials, the compound shown in Table 11 (13 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 529

[1152] By using the compound obtained in Example 461, (1) (17 mg) and the compound obtained in Reference Example 70 (17 mg) as starting materials, the compound shown in Table 11 (13.5 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 530

[1153] By using the compound obtained in Example 461, (1) (20 mg) and the compound obtained in Reference Example 71 (11 mg) as starting materials, the compound shown in Table 11 (14 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 531

[1154] The compound obtained in Reference Example 192 (31.1 mg) was dissolved in dichloromethane (622 µl), the solution was added with the Dess-Martin reagent (79.2 mg), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate (1:1), the layers were separated, and the organic layer was concentrated under reduced pressure to obtain an aldehyde compound. By using the resulting aldehyde compound and the amine compound obtained in Example 262, (2) (30 mg) of which steric configuration of the 4"-position was S as starting materials, the compound shown in Table 11 (2.3 mg) was obtained in the same manners as those of Example 7, (2) and Example 7, (4).

Example 532

[1155] By using the compound obtained in Example 368, (1) (30 mg) and the compound obtained in Reference Example 71 (45 mg) as starting materials, the compound shown in Table 11 (33 mg) was obtained in the same manner as that of Example 168, (2).

Example 533

[1156] By using the compound obtained in Example 368, (1) (20 mg) and the compound obtained in Reference Example 70 (30 mg) as starting materials, the compound shown in Table 11 (20 mg) was obtained in the same manner as that of Example 168, (2).

Example 534

[1157] 

(1) The compound obtained in Example 461, (1) (60 mg) was dissolved in dimethylformamide (1.5 ml), the solution was added with the compound obtained in Reference Example 193 (20.1 mg) and sodium t-butoxide (1.7 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and then the organic layer was washed with distilled water. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:triethylamine = 30:10:0.2) to obtain a carbamate compound (51.1 mg).

(2) By using the compound obtained in (1) mentioned above (51.1 mg) as a starting material, the compound shown in Table 11 (17.1 mg) was obtained in the same manner as that of Example 7, (4).

Example 535

[1158] The compound obtained in Example 412, (1) (23 mg) and (1S)-(2-methoxyphenyl)ethanamine (24 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) were dissolved in ethanol (0.3 ml), the solution was added with potassium iodide (26 mg), and the mixture was stirred at 120°C for 30 minutes under microwave irradiation. The reaction mixture was added with ethyl acetate, and the mixture was filtered. Then, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (hexane:acetone:28% aqueous ammonia=5:5:0.1) to obtain the compound shown in Table 11 (19 mg).

Example 536

[1159] By using the compound obtained in Example 412, (1) (23 mg) and 2-methoxybenzylamine (18 µl) as starting materials, the compound shown in Table 11 (10 mg) was obtained in the same manner as that of Example 535.

Example 537

[1160] By using the compound obtained in Example 412, (1) (21 mg) and benzylamine (16 µl) as starting materials, the compound shown in Table 11 (17 mg) was obtained in the same manner as that of Example 535.

Example 538

[1161] By using the compound obtained in Example 412, (1) (25 mg) and (1S,2S)-thiomicamine (36 mg) as starting materials, the compound shown in Table 11 (25 mg) was obtained in the same manner as that of Example 535.

Example 539

[1162] By using the compound obtained in Example 412, (1) (25 mg) and (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (36 mg) as starting materials, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 535.

Example 540

[1163] By using the compound obtained in Example 412, (1) (25 mg) and (1S,2S)-2-amino-1-phenyl-1,3-propanediol (29 mg) as starting materials, the compound shown in Table 11 (26 mg) was obtained in the same manner as that of Example 535.

Example 541

[1164] By using the compound obtained in Example 412, (1) (25 mg) and (R)-2-amino-1-phenylethanol (23 mg) as starting materials, the compound shown in Table 11 (25 mg) was obtained in the same manner as that of Example 535.

Example 542

[1165] By using the compound obtained in Example 412, (1) (25 mg) and L-phenylalaninol (26 mg) as starting materials, the compound shown in Table 11 (23 mg) was obtained in the same manner as that of Example 535.

Example 543

[1166] 

(1) The compound obtained in Example 405, (1) (20 mg) and the compound obtained in Reference Example 194 (15 mg) were dissolved in dimethylformamide (0.1 ml), and the solution was stirred at 90°C for 4 hours. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was washed successively with distilled water and saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol=15:1) to obtain a urea compound (22 mg).

(2) By using the compound obtained in (1) mentioned above (22 mg) as a starting material, the compound shown in Table 11 (15 mg) was obtained in the same manner as that of Example 7, (4).

Example 544

[1167] 

(1) By using the compound obtained in Example 405, (1) (28.2 mg) and the compound obtained in Reference Example 195 (12.7 mg) as starting materials, the compound shown in Table 11 (3.6 mg) was obtained in the same manners as those of Example 112, (2) and Example 7, (4).

Example 545

[1168] By using the amine compound obtained in Example 262, (2) (60 mg) of which steric configuration of the 4"-position was S and the compound obtained in Reference Example 196 (29.9 mg) as starting materials, the compound shown in Table 11 (7.5 mg) was obtained in the same manners as those of Example 524, (1), Example 522, (2), Example 524 (3) and Example 7, (4).

Example 546

[1169] By using the compound obtained in Example 412, (1) (20 mg) and the compound obtained in Reference Example 54, (2) (20 mg) as starting materials, the compound shown in Table 11 (8 mg) was obtained in the same manner as that of Example 535.

Example 547

[1170] By using the compound obtained in Example 412, (1) (23 mg) and 4-methoxyphenetylamine (21 µl) as starting materials, the compound shown in Table 11 (20 mg) was obtained in the same manner as that of Example 535.

Example 548

[1171] By using the compound obtained in Example 412, (1) (22 mg) and 2-methoxyphenetylamine (21 µl) as starting materials, the compound shown in Table 11 (17 mg) was obtained in the same manner as that of Example 535.

Example 549

[1172] By using the compound obtained in Example 412, (1) (23 mg) and phenetylamine (20 µl) as starting materials, the compound shown in Table 11 (19 mg) was obtained in the same manner as that of Example 535.

Example 550

[1173] By using the compound obtained in Example 412, (1) (29 mg) and the compound obtained in Reference Example 197 (36 mg) as starting materials, the compound shown in Table 11 (30 mg) was obtained in the same manner as that of Example 535.

Example 551

[1174] By using the compound obtained in Example 412, (1) (28 mg) and the compound obtained in Reference Example 198 (24 mg) as starting materials, the compound shown in Table 11 (31 mg) was obtained in the same manner as that of Example 535.

Syntheses of Examples 552 to 558

[1175] Preparation methods of compounds represented by the formula (X) having R defined in Table 12 are shown below.

[Table 12-1]

[1176] 

Table 12

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
552		769	(300 MHz) : 0.84 - 0.91 (m, 9 H) 1.00 (d, J=6.9 Hz, 3 H) 1.09 - 1.15 (m, 4 H) 1.19 (d, J=6.0 Hz, 1 H) 1.26 (s, 3 H) 1.51 - 1.60 (m, 4 H) 1.92 (m, 1 H) 2.22 - 2.30 (m, 8 H) 2.38 (s, 3 H) 2.47 - 2.52 (m, 3 H) 2.83 (m, 1 H) 3.02 (d, J=14.1 Hz, 1 H) 3.18 - 3.23 (m, 5 H) 3.35 (m, 1 H) 3.61 (d, J=16.4 Hz, 1 H) 3.71 (d, J=16.4 Hz, 1 H) 3.82 - 3.93 (m, 10 H) 4.09 (m, 1 H) 4.72 (m, 1 H) 5.26 (m, 1 H), 6.62 (d, J=8.7 Hz, 1 H), 6.92 (d, J=8.7 Hz, 1 H)
553		704	(300 MHz): 0.83 - 0.94 (m, 12 H) 1.08 (d, J=7.2 Hz, 3 H) 1.18 (d, J=6.0 Hz, 3 H) 1.22 - 1.30 (m, 4 H) 1.50 - 1.60 (m, 4 H) 1.91 (m, 1 H) 2.17 - 2.28 (m, 8 H) 2.38 (s, 3 H) 2.44 - 2.52 (m, 3 H) 2.83 (q, J=7.2 Hz, 1 H) 3.02 (d, J=14.4 Hz, 1 H) 3.15 - 3.27 (m, 6 H) 3.70 - 3.76 (m, 3 H) 3.81 (d, J=3.9 Hz, 1 H) 4.02 (m, 1 H) 4.69 (m, 1 H) 7.46 (d, J=8.1 Hz, 2 H), 7.62 (d, J=8.1 Hz, 2 H)
554		704 FAB MASS	(400 MHz): 0.84 - 0.91 (m, 9 H) 0.96 (d, J=6.8 Hz, 3 H) 1.09 (d, J=7.3 Hz, 3 H) 1.19 (d, J=6.1 Hz, 3 H) 1.23 - 1.27 (m, 4 H) 1.53 - 1.67 (m, 4 H) 1.91 (m, 1 H) 2.15 - 2.25 (m, 2 H) 2.32 (s, 6 H) 2.39 (s, 3 H) 2.42 - 2.50 (m, 3 H) 2.85 (t, J=7.8 Hz, 1 H) 3.04 (d, J=14.6 Hz, 1 H) 3.17 - 3.28 (m, 6 H) 3.70 - 3.78 (m, 3 H) 3.83 (d, J=4.1 Hz, 1 H) 4.07 (m, 1 H) 4.69 (m, 1 H) 5.36 (m, 1 H) 7.45 (dd, J=7.8 Hz, J=7.8 Hz, 1 H) 7.57 - 7.60 (m, 2 H) 7.64 (s, 1 H)

[1177] 

[Table 12-2]

555		757 FAB MASS	(400 MHz) : 0.84 - 0.90 (m, 9 H) 0.96 (d, J=6.8 Hz, 3 H) 1.06 (d, J=6.8 Hz, 3 H) 1.19 (d, J=6.1 Hz, 3 H) 1.23 - 1.27 (m, 4 H) 1.51 - 1.68 (m, 4 H) 1.89 -1.92 (m, 1 H) 2.19 - 2.25 (m, 2 H) 2.30 (s, 6 H) 2.38 - 2.51 (m, 6 H) 2.81 - 2.87 (m, 1 H) 3.03 - 3.07 (m, 4 H) 3.17 - 3.23 (m, 5 H) 3.28 - 3.29 (m, 1 H) 3.81 - 3.84 (m, 4 H) 4.05 - 4.07 (m, 1 H) 4.70 (m, H) 5.35 (m, 1 H) 7.55 (dd, J=7.7 Hz, J=7.7 Hz, 1 H) 7.62 (d, J=7.7 Hz, 1 H), 7.87 (d, J=7.7 Hz, 1 H) 7.93 (s, 1 H)
556		694	(300 MHz): 0.82 - 0.95 (m, 12 H) 1.07 - 1.27 (m, 2 H) 1.11 (d, J=7.15 Hz, 3 H) 1.14 (d, J=5.76 Hz, 3 H) 1.25 (s, 3 H) 1.45 - 1.95 (m, 4 H) 2.10 - 2.39 (m, 3 H) 2.27 (s, 6 H) 2.38 (s, 3 H) 2.43 - 2.59 (m, 2 H) 2.76 - 2.89 (m, 1 H) 2.93 - 3.08 (m, 2 H) 3.14 (dd, J=2.75, 9.89 Hz, 2 H) 3.20 (s , 3 H) 3.60 (d, J=14.01 Hz, 1 H) 3.68 (d, J=14.01 Hz, 1 H) 4.64 - 4.79 (m, 1 H) 5.15 - 5.33 (m, 1 H) 6.69 - 6.75 (m, 2 H) 7.04 - 7.13 (m, 2 H)
557		694	(300 MHz): 0.82 - 1.02 (m, 12 H) 1.05 - 1.27 (m, 2 H) 1.09 (d, J=7.14 Hz, 3 H) 1.16 (d, J=6.32 Hz, 3 H) 1.25 (s, 3 H) 1.40 - 2.58 (m, 9 H) 2.33 (s, 6 H) 2.39 (s, 3 H) 2.72 - 2.86 (m, 1 H) 2.96 - 3.23 (m, 4H) 3.20 (s, 3H) 3.59 (s, 2H) 3.87 (d, J=4.12 Hz, 1 H) 3.94 - 4.06 (m, 1 H) 4.63 - 4.78 (m, 1 H) 5.23 - 5.31 (m, 1 H) 6.55 - 6.61 (m, 1 H) 6.69 (d, J=7.42 Hz, 1 H) 6.71 (s , 1 H) 7.09 (t, J=7.69 Hz, 1 H)
558		694	(300 MHz) : 0.82 - 0.97 (m, 12 H) 1.16 - 1.27 (m, 2 H) 1.09 (d, J=7.42 Hz, 3 H) 1.16 (d, J=6.32 Hz, 3 H) 1.25 (s, 3 H) 1.45 - 1.98 (m, 4 H) 2.11 - 2.58 (m, 5 H) 2.30 (s, 6 H) 2.38 (s, 3 H) 2.75 - 2.87 (m, 1 H) 2.96 - 3.22 (m, 4 H) 3.21 (s, 3 H) 3.54 (d, J=15.39 Hz, 1 H) 3.59 (d, J=15.11 Hz, 1 H) 3.85 (d, J=4.12 Hz, 1 H) 3.96 (d, J=6.60 Hz, 1 H) 4.66 - 4.79 (m, 1 H) 5.12 - 5.31 (m, 1 H) 6.62 - 6.66 (m, 2 H) 7.12 (d, J=8.52 Hz, 2 H)

Example 552

[1178] By using the compound obtained in Example 112, (1) (50 mg) and 2,3,4-trimethoxyphenylacetic acid (47 mg) as starting materials, the compound shown in Table 12 (2.5 mg) was obtained in the same manners as those of Example 112, (2) and Example 7, (4).

Example 553

[1179] By using the compound obtained in Example 112, (1) (50 mg) and 4-cyanophenylacetic acid (34 mg) as starting materials, the compound shown in Table 12 (2.6 mg) was obtained in the same manners as those of Example 112, (2) and Example 7, (4).

Example 554

[1180] 

(1) The compound obtained in Example 112, (1) (50 mg) was dissolved in dichloromethane (0.5 ml), the solution was added with 3-cyanophenylacetic acid (68 mg), dicyclohexylcarbodiimide (86 mg) and 4-dimethylaminopyridine (17.0 mg), and the mixture was stirred at room temperature for 3 days. The reaction mixture was added with saturated aqueous ammonium chloride and chloroform, the layers were separated, and then the organic layer was filtered by using a phase separator. The filtrate was washed with saturated aqueous sodium hydrogencarbonate, and filtered by using a phase separator, and then the filtrate was concentrated under reduced pressure, the residue was added with methanol, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=15:1:0.1) to obtain an acyl compound (18.5 mg).

(2) By using the compound obtained in (1) mentioned above (18.5 mg) as a starting material, the compound shown in Table 12 (8.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 555

[1181] By using the compound obtained in Example 112, (1) (50 mg) and 3-methanesulfonylphenylacetic acid (90 mg) as starting materials, the compound shown in Table 12 (15.4 mg) was obtained in the same manners as those of Example 554, (1) and Example 7, (4).

Example 556

[1182] 

(1) The compound obtained in Example 112, (1) (50 mg) was dissolved in dimethylformamide (1.0 ml), the solution was added with dicyclohexylcarbodiimide (120 mg), 4-dimethylaminopyridine (26.1 mg) and 2-(2-nitrophenyl)acetic acid (114 mg), and the mixture was stirred at room temperature for 3 days. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was added with methanol (5 ml). The mixture was stirred at room temperature for 24 hours, and then concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a condensed compound (41 mg).

(2) By using the compound obtained in (1) mentioned above (41 mg) as a starting material, a detriethylsilylated compound (15.4 mg) was obtained in the same manner as that of Example 7, (4).

(3) The compound obtained in (2) mentioned above (15.4 mg) was dissolved in methanol-ethyl acetate (1:1, 2.0 ml), the solution was added with 10% palladium-carbon (3 mg), and the mixture was stirred at room temperature for 4 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through Celite, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 12 (7.3 mg).

Example 557

[1183] By using the compound obtained in Example 112, (1) (50 mg) and 2-(3-nitrophenyl)acetic acid (114 mg) as starting materials, the compound shown in Table 12 (1.5 mg) was obtained in the same manners as those of Example 556, (1), Example 7, (4) and Example 556 (3).

Example 558

[1184] By using the compound obtained in Example 112, (1) (50 mg) and 2-(4-nitrophenyl)acetic acid (114 mg) as starting materials, the compound shown in Table 12 (4.8 mg) was obtained in the same manners as those of Example 556, (1) Example 7, (4) and Example 556, (3).

Example 559: Synthesis of the compound represented by the formula (Y)

[1185] 

[1186] By using the compound obtained in Example 195 (8 mg) and 2-chloroethanesulfonyl chloride (2 µl) as starting materials, the title compound (8 mg) was obtained in the same manner as that of Example 196.

Syntheses of Examples 560 to 562

[1187] Preparation methods of compounds represented by the formula (Z) having R defined in Table 13 are shown below.

[Table 13]

[1188] 

Table 13

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
560		786.5	(500 MHz):0.87 (t, J=7.54 Hz, 3 H) 1.06 (d, J=6.86 Hz, 3 H) 1.08 (d, J=7.68 Hz, 3 H) 1.11 (d, J=6.86 Hz, 3 H) 1.16 (d, J=7.13 Hz, 3 H) 1.21 (d, J=6.31 Hz, 3 H) 1.23 (s, 3 H) 1.23 - 1.25 (m, 4 H) 1.28 (s, 3 H) 1.50 - 1.67 (m, 5 H) 1.73 (s, 3 H) 1.92 - 2.00 (m, 1 H) 2.01 - 2.08 (m, 1 H) 2.13 (s, 3 H) 2.15 (d, J=10.42 Hz, 1 H) 2.28 (s, 6 H) 2.38 (d, J=15.08 Hz, 1 H) 2.42 - 2.50 (m, 1 H) 2.51 - 2.59 (m, 1 H) 2.68 - 2.75 (m, 2 H) 3.00 (t, J=9.87 Hz, 1 H) 3.20 (s, 3 H) 3.25 - 3.32 (m, 1 H) 3.32 (s, 3 H) 3.38 - 3.45 (m, 1 H) 3.47 - 3.57 (m, 2 H) 3.67 (d, J=6.86 Hz, 1 H) 3.88 (d, J=4.11 Hz, 1 H) 3.97 - 4.04 (m, 1 H) 4.41 (s, 2 H) 4.47 (d, J=7.40 Hz, 1 H) 4.80 (br. s., 1 H) 4.84 (s, 1 H) 4.89 (d, J=4.66 Hz, 1 H) 4.94 (s, 1 H)
561		746.4	(500 MHz):0.88 (t, J=7.40 Hz, 3 H) 1.06 (d, J=6.86 Hz, 3 H) 1.07 - 1.09 (m, 3 H) 1.08-1.11 (m, 3H) 1.16 (d, J=7.13 Hz, 3H) 1.19 -1.30 (m, 10H) 1.27 (s, 3H) 1.48 - 1.68 (m, 5 H) 1.89 (d, J=14.81 Hz, 1 H) 1.99 - 2.06 (m, 1 H) 2.11 (s, 3 H) 2.14 (d, J=10.42 Hz, 1 H) 2.28 (s, 6 H) 2.38 (d, J=15.36 Hz, 1 H) 2.43 - 2.51 (m, 1 H) 2.54 - 2.61 (m, 1 H) 2.67 - 2.75 (m, 2 H) 2.97 - 3.03 (m, 1 H) 3.21 (s, 3 H) 3.28 - 3.32 (m, 1 H) 3.33 (s, 3 H) 3.38 - 3.45 (m, 1 H) 3.47 - 3.56 (m, 2 H) 3.67 (d, J=6.86 Hz, 1 H) 3.78 (s, 3 H) 3.86 - 3.91 (m, 1 H) 4.01 (d, 1 H) 4.47 (d, J=7.40 Hz, 1 H) 4.79 - 4.86 (m, 1 H) 4.89 (d, J=4.66 Hz, 1 H)
562		776.4	(500 MHz):0.87 (t, J=7.54 Hz, 3 H) 1.08 (dd, J=6.99, 3.70 Hz, 6 H) 1.12 (d, J=6.86 Hz, 3 H) 1.16 (d, J=7.13 Hz, 3 H) 1.18 - 1.27 (m, 1 H) 1.21 (d, J=6.03 Hz, 3 H) 1.23 (s, 3 H) 1.24 (d, J=6.31 Hz, 3 H) 1.30 (s, 3 H) 1.47 - 1.67 (m, 5 H) 1.99 - 2.06 (m, 1 H) 2.06 -2.12 (m, 1 H) 2.14 -2.17 (m, 1 H) 2.17 (s, 3 H) 2.28 (s, 6 H) 2.35 - 2.40 (m, 1 H) 2.41 - 2.49 (m, 1 H) 2.49 - 2.56 (m, 1 H) 2.65 - 2.80 (m, 2 H) 3.00 (t, J=9.87 Hz, 1 H) 3.22 (s, 3 H) 3.25 - 3.31 (m, 1 H) 3.32 (s, 3 H) 3.41 (s, 3 H) 3.41 - 3.46 (m, 1 H) 3.47 - 3.56 (m, 2 H) 3.67 (d, J=7.13 Hz, 1 H) 3.85 - 3.90 (m, 1 H) 3.97 - 4.05 (m, 1 H) 4.46 (d, J=7.13 Hz, 1 H) 4.78 (br. s., 1 H) 4.89 (d, J=4.39 Hz, 1 H) 5.03 -5.10 (m, 2H)

Example 560

[1189] The compound obtained in Example 214 (101 mg) was dissolved in tetrahydrofuran (6 ml), the solution was added with 3-chloro-2-methyl-1-propene (41 µl), potassium hydroxide (77.4 mg) and 18-crown-6-ether (365 mg), and the mixture was stirred at room temperature 15 minutes. The reaction mixture was added with saturated brine and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 9:1 to chloroform:methanol:28% aqueous ammonia = 10:1:0.1) and preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 13 (33.8 mg).

Example 561

[1190] The compound obtained in Example 214 (104 mg) was dissolved in tetrahydrofuran (6 ml), the solution was added with methyl iodide (9 µl) and potassium hydroxide (23.9 mg), and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was added with saturated brine and chloroform, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 13 (62.8 mg).

Example 562

[1191] By using the compound obtained in Example 214 (104 mg) and chloromethyl methyl ether (32.4 µl) as starting materials, the compound shown in Table 13 (44.0 mg) was obtained in the same manner as that of Example 560.

Syntheses of Examples 563 to 566

[1192] Preparation methods of compounds represented by the formula (AA) having R defined in Table 14 are shown below.

[Table 14-1]

[1193] 

Table 14

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
563		803.5	(600 MHz):0.73 - 0.84 (m, 6 H) 0.88 (t, J=7.34 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.10 - 1.14 (m, 1 H) 1.16 (d, J=7.79 Hz, 3 H) 1.19 - 1.23 (m, 6 H) 1.23 - 1.26 (m, 1 H) 1.28 (d, J=5.96 Hz, 3 H) 1.32 (s, 3 H) 1.44 - 1.50 (m, 1 H) 1.53 (dd, J=15.13, 5.04 Hz, 1 H) 1.63 - 1.86 (m, 3 H) 2.20 - 2.33 (m, 9 H) 2.35 (d, J=15.13 Hz, 1 H) 2.46 - 2.56 (m, 2 H) 2.76 - 2.85 (m, 1 H) 2.94 - 3.02 (m, 2 H) 3.17 - 3.25 (m, 2 H) 3.21 (s, 3 H) 3.31 (s, 3 H) 3.37 - 3.58 (m, 3 H) 3.69 (d, J=7.79 Hz, 1 H) 3.72 (s, 3 H) 4.01 - 4.08 (m, 1 H) 4.09 - 4.20 (m, 1 H) 4.36 (d, J=6.88 Hz, 1 H) 4.56 - 4.68 (m, 1 H) 4.93 (d, J=4.58 Hz, 1 H) 5.98 (d, J=16.05 Hz, 1 H) 6.87 - 6.95 (m, 1 H)

[1194] 

[Table 14-2]

564		820.5	(600 MHz):0.51 - 0.65 (m, 3 H) 0.74 - 0.84 (m, 6 H) 0.99 - 1.03 (m, 1 H) 1.04 (d, J=7.34 Hz, 3 H) 1.12 (d, J=7.34 Hz, 3 H) 1.15 (d, J=5.96 Hz, 3 H) 1.17 (s, 3 H) 1.17 - 1.19 (m, 1 H) 1.23 (d, J=5.96 Hz, 3 H) 1.26 (s, 3 H) 1.34 - 1.44 (m, 2 H) 1.48 (dd, J=15.36, 4.81 Hz, 1 H) 1.56 - 1.66 (m, 2 H) 1.68 - 1.81 (m, 1 H) 2.07 - 2.18 (m, 1 H) 2.23 (s, 6 H) 2.25 - 2.27 (m, 1 H) 2.30 (d, J=15.13 Hz, 1 H) 2.33 - 2.46 (m, 3 H) 2.73 - 2.80 (m, 1 H) 2.91 - 2.99 (m, 2 H) 3.09 - 3.15 (m, 1 H) 3.17 (s, 3 H) 3.26 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.49 - 3.55 (m, 1 H) 3.65 (d, J=7.79 Hz, 1 H) 3.70 (s, 2 H) 3.96 - 4.02 (m, 1 H) 4.08 - 4.13 (m, 1 H) 4.30 (d, J=7.34 Hz, 1 H) 4.58 - 4.67 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 7.44 (d, J=8.25 Hz, 2 H) 7.53 (d, J=8.25 Hz, 2 H)
565		867.5	(600 MHz):0.50 - 0.59 (m, 3 H) 0.71 - 0.77 (m, 3 H) 0.78 - 0.85 (m, 3 H) 0.94 - 1.00 (m, 1 H) 1.03 (d, J=7.34 Hz, 3 H) 1.12 (d, J=7.79 Hz, 3 H) 1.13 - 1.19 (m, 9 H) 1.20 - 1.31 (m, 2 H) 1.23 (d, J=6.42 Hz, 3 H) 1.25 (s, 2 H) 1.41 - 1.82 (m, 3 H) 1.99 - 2.59 (m, 7 H) 2.23 (s, 6 H) 2.30 (d, J=15.13 Hz, 1 H) 2.74 - 2.83 (m, 1 H) 2.93 - 2.98 (m, 2 H) 3.09 - 3.15 (m, 1 H) 3.16 (s, 3 H) 3.26 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.45 - 3.52 (m, 1 H) 3.53 (s, 2 H) 3.61 (s, 3 H) 3.62 - 3.71 (m, 3 H) 3.95 - 4.03 (m, 1 H) 4.11 - 4.16 (m, 1 H) 4.30 (d, J=6.88 Hz, 1 H) 4.56 - 4.62 (m, 1 H) 4.90 (d, J=4.59 Hz, 1 H) 7.15 (d, J=7.79 Hz, 1 H) 7.25 (d, J=7.79 Hz, 2 H)
566		789.5	(600 MHz):0.75 - 0.83 (m, 6 H) 0.84 - 0.91 (m, 3 H) 1.03 - 1.13 (m, 6 H) 1.16 (d, J=7.34 Hz, 3 H) 1.20 - 1.36 (m, 9 H) 1.45 - 2.17 (m, 5 H) 1.53 (dd, J=14.90, 4.81 Hz, 1 H) 2.23 - 2.43 (m, 4 H) 2.45 - 2.72 (m, 8 H) 2.77 - 2.91 (m, 2 H) 2.95 - 2.99 (m, 1 H) 3.00 (d, J=9.63 Hz, 1 H) 3.16 - 3.19 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.48 (m, 3 H) 3.45 - 3.55 (m, 1 H) 3.69 (d, J=8.25 Hz, 1 H) 3.99 - 4.07 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.41 (d, J=6.88 Hz, 1 H) 4.56 - 4.69 (m, 1 H) 4.92 (d, J=4.58 Hz, 1 H) 5.93 - 6.04 (m, 1 H) 6.79 - 6.91 (m, 1 H)

Example 563

[1195] 

(1) The compound obtained in Example 245, (2) (200 mg) was dissolved in dimethylformamide (3.8 ml), the solution was added with methyl 4-bromocrotonate (265 µl) and potassium carbonate (260 mg), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added with distilled water and diethyl ether, and the layers were separated. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform to hexane:acetone:triethylamine = 10:10:0.2) to obtain an N-alkyl compound (70 mg).

(2) By using the compound obtained in (1) mentioned above (70 mg) as a starting material, the compound shown in Table 14 (49 mg) was obtained in the same manner as that of Example 7, (4).

Example 564

[1196] By using the compound obtained in Example 245, (2) (200 mg) and 4-cyanobenzyl bromide (370 mg) as starting materials, the compound shown in Table 14 (53 mg) was obtained in the same manners as those of Example 563, (1) and Example 7, (4).

Example 565

[1197] By using the compound obtained in Example 245, (2) (200 mg) and 4-(bromomethyl)phenylacetic acid methyl ester (460 mg) as starting materials, the compound shown in Table 14 (14 mg) was obtained in the same manners as those of Example 563, (1) and Example 7, (4).

Example 566

[1198] The compound obtained in Example 563, (2) (27 mg) was dissolved in a mixed solvent of tetrahydrofuran-methanol-distilled water (3:1:1, 1 ml), the solution was added with lithium hydroxide monohydrate (7 mg), and the mixture was stirred at room temperature for 4 hours. The mixture was further added with lithium hydroxide monohydrate (7 mg), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was added with chloroform and saturated aqueous ammonium chloride, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 3:1:0.1) to obtain the compound shown in Table 14 (3 mg).

Syntheses of Examples 567 to 663

[1199] Preparation methods of compounds represented by the formula (AB) having R defined in Table 15 are shown below.

[Table 15-1]

[1200] 

Table 15

Example	R	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
567		852.6	(500 MHz):0.78 - 0.86 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 - 1.25 (m, 2 H) 1.15 (d, J=7.40 Hz, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.55 - 1.68 (m, 4 H) 1.79 - 1.89 (m, 2 H) 2.22 - 2.31 (m, 4 H) 2.27 (s, 6 H) 2.32 - 2.37 (m, 1 H) 2.35 (s, 3 H) 2.41 - 2.50 (m, 2 H) 2.74 - 2.83 (m, 1 H) 2.88 - 2.94 (m, 1 H) 3.00 (t, J=9.32 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.56 (m, 4 H) 3.69 (d, J=7.95 Hz, 1 H) 3.98 - 4.08 (m, 1 H) 4.07 - 4.16 (m, 1 H) 4.39 (d, J=7.13 Hz, 1 H) 4.69 - 4.82 (m, 1 H) 4.91 (d, J=4.39 Hz, 1 H) 6.36 (br. s., 1 H) 7.39 - 7.44 (m, 2 H) 7.45 - 7.50 (m, 1 H) 7.71 - 7.78 (m, 2 H)
568		853.6	(500 MHz):0.79 - 0.87 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.15 (d, J=7.40 Hz, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.57 (m, 1 H) 1.56 - 1.71 (m, 4 H) 1.76 - 1.93 (m, 2 H) 2.15 - 2.29 (m, 4 H) 2.27 (s, 6 H) 2.32 - 2.38 (m, 1 H) 2.35 (s, 3 H) 2.41 - 2.52 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.88 - 2.95 (m, 1 H) 3.00 (t, J=9.74 Hz, 1 H) 3.20 (dd, J=10.28, 7.27 Hz, 1 H) 3.23 (s, 3 H) 3.26 - 3.29 (m, 1 H) 3.31 (s, 3 H) 3.34 - 3.51 (m, 2 H) 3.51 - 3.60 (m, 1 H) 3.69 (d, J=7.95 Hz, 1 H) 4.00 - 4.07 (m, 1 H) 4.07 - 4.14 (m, 1 H) 4.39 (d, J=7.40 Hz, 1 H) 4.75 - 4.85 (m, 1 H) 4.90 (d, J=4.66 Hz, 1 H) 6.58 (br. s., 1 H) 7.34 - 7.40 (m, 1 H) 8.07 - 8.15 (m, 1 H) 8.70 (dd, J=4.94, 1.65 Hz, 1 H) 8.97 (d, J=1.65 Hz, 1 H)
569		903.7	(500 MHz):0.75 - 0.90 (m, 6 H) 1.08 (d, J=7.65 Hz, 3 H) 1.14 (d, J=7.65 Hz, 3 H) 1.16 - 1.28 (m, 2 H) 1.20 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.29, 4.59 Hz, 1 H) 1.58 - 1.91 (m, 6 H) 2.13 - 2.30 (m, 4 H) 2.28 (s, 6 H) 2.33 (d, J=15.29 Hz, 1 H) 2.38 (s, 3 H) 2.41 - 2.51 (m, 2 H) 2.73 - 2.85 (m, 1 H) 2.91 - 2.97 (m, 1 H) 3.00 (t, J=9.56 Hz, 1 H) 3.16 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.34 - 3.43 (m, 1 H) 3.43 - 3.49 (m, 1 H) 3.49 - 3.64 (m, 2 H) 3.69 (d, J=8.41 Hz, 1 H) 4.01 - 4.08 (m, 1 H) 4.08 - 4.15 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.74 - 4.85 (m, 1 H) 4.90 (d, J=4.59 Hz, 1 H) 6.28 (br. s., 1 H) 7.46 (dd, J=8.79, 4.20 Hz, 1 H) 7.62 - 7.71 (m, 2 H) 8.13 - 8.19 (m, 1 H) 8.74 (d, J=8.41 Hz, 1 H) 8.92 - 8.96 (m, 1 H)

[1201] 

[Table 15-2]

570		903.7	(500 MHz):0.75 - 0.86 (m, 6 H) 1.07 (d, J=6.88 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.14 (d, J=7.65 Hz, 3 H) 1.17 - 1.24 (m, 6 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.29, 4.59 Hz, 1 H) 1.60 - 1.74 (m, 4 H) 1.78 - 1.90 (m, 2 H) 2.16 - 2.30 (m, 4 H) 2.28 (s, 6 H) 2.33 (d, J=14.53 Hz, 1 H) 2.38 (s, 3 H) 2.42 - 2.52 (m, 2 H) 2.75 - 2.84 (m, 1 H) 2.91 - 3.03 (m, 2 H) 3.14 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.30 (s, 3 H) 3.33 - 3.41 (m, 1 H) 3.43 - 3.49 (m, 1 H) 3.49 - 3.64 (m, 2 H) 3.69 (d, J=8.41 Hz, 1 H) 3.98 - 4.08 (m, 1 H) 4.08 - 4.16 (m, 1 H) 4.38 (d, J=7.65 Hz, 1 H) 4.76 - 4.85 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 6.22 - 6.37 (m, 1 H) 7.56 - 7.62 (m, 1 H) 7.83 (d, J=6.88 Hz, 1 H) 8.04 (d, J=8.41 Hz, 1 H) 8.15 (d, J=6.12 Hz, 1 H) 8.57 (d, J=6.12 Hz, 1 H) 9.26 (s, 1 H)
571		842.6	(500 MHz):0.78 - 0.88 (m, 6 H) 1.09 (d, J=6.88 Hz, 3 H) 1.16 (d, J=7.65 Hz, 3 H) 1.15 - 1.26 (m, 2 H) 1.21 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.47 - 1.67 (m, 5 H) 1.72 - 1.83 (m, 1 H) 1.83 - 1.90 (m, 1 H) 2.13 - 2.31 (m, 4 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.35 - 2.39 (m, 1 H) 2.41 - 2.51 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.88 - 2.95 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.16 - 3.23 (m, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.33 - 3.40 (m, 2 H) 3.43 - 3.52 (m, 2 H) 3.70 (d, J=7.65 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.08 - 4.17 (m, 1 H) 4.40 (d, J=7.65 Hz, 1 H) 4.73 - 4.84 (m, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 6.12 (br. s., 1 H) 6.64 (s, 1 H) 7.39 - 7.44 (m, 1 H) 7.94 (s, 1 H)
572		858.6	(500 MHz):0.73 - 0.84 (m, 6 H) 1.11 (d, J=7.26 Hz, 3 H) 1.19 - 1.31 (m, 2 H) 1.19 - 1.22 (m, 3 H) 1.22 (d, J=6.12 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.53 - 1.57 (m, 1 H) 1.63 - 1.71 (m, 1 H) 1.79 - 1.87 (m, 1 H) 1.87 - 1.96 (m, 1 H) 2.04 - 2.12 (m, 1 H) 2.22 - 2.38 (m, 5 H) 2.30 (s, 6 H) 2.35 (s, 3 H) 2.38 - 2.45 (m, 1 H) 2.46 - 2.54 (m, 1 H) 2.82 - 2.89 (m, 1 H) 2.94 - 3.05 (m, 2 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.38 - 3.44 (m, 1 H) 3.44 - 3.51 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.78 - 3.87 (m, 1 H) 3.93 - 4.01 (m, 1 H) 4.02 - 4.10 (m, 1 H) 4.14 - 4.21 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.67 - 4.75 (m, 1 H) 4.94 (d, J=4.20 Hz, 1 H) 6.10 - 6.16 (m, 2 H) 6.58 - 6.63 (m, 2 H)
573		854.7	(500 MHz):0.77 - 0.85 (m, 6 H) 1.08 (d, J=7.65 Hz, 3 H) 1.10 - 1.24 (m, 2 H) 1.15 (d, J=7.65 Hz, 3 H) 1.19 - 1.24 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.29, 4.59 Hz, 1 H) 1.56 - 1.74 (m, 4 H) 1.79 - 1.89 (m, 2 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.37 (m, 4 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.39 - 2.51 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.90 - 2.96 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.17 - 3.21 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.54 (m, 4 H) 3.69 (d, J=7.65 Hz, 1 H) 3.96 - 4.09 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.38 (d, J=6.88 Hz, 1 H) 4.68 - 4.82 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 7.81 - 7.89 (m, 1 H) 8.51 - 8.55 (m, 1 H) 8.74 (d, J=3.06 Hz, 1 H) 9.37 - 9.41 (m, 1 H)

[1202] 

[Table 15-3]

574		904.7	(500 MHz):0.74 - 0.90 (m, 6 H) 1.07 (d, J=7.65 Hz, 3 H) 1.09 - 1.26 (m, 2 H) 1.13 (d, J=7.65 Hz, 3 H) 1.19 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.12 Hz, 3 H) 1.30 (s, 3 H) 1.52 (dd, J=14.91, 4.97 Hz, 1 H) 1.64 (d, J=13.00 Hz, 1 H) 1.66 - 1.95 (m, 5 H) 2.17 - 2.36 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.41 - 2.51 (m, 2 H) 2.74 - 2.84 (m, 1 H) 2.91 - 3.04 (m, 2 H) 3.16 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.31 - 3.40 (m, 1 H) 3.40 - 3.51 (m, 1 H) 3.54 - 3.66 (m, 2 H) 3.68 (d, J=7.65 Hz, 1 H) 3.94 - 4.13 (m, 2 H) 4.38 (d, J=6.88 Hz, 1 H) 4.76 - 4.85 (m, 1 H) 4.87 (d, J=4.59 Hz, 1 H) 6.76 - 7.03 (m, 1 H) 7.82 (t, J=8.41 Hz, 1 H) 7.85 - 7.89 (m, 1 H) 8.32 (d, J=7.65 Hz, 1 H) 8.52 (d, J=9.17 Hz, 1 H) 9.27 (s, 1 H)
575		854.7	(500 MHz):0.76 - 0.91 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 - 1.24 (m, 2 H) 1.15 (d, J=7.13 Hz, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.23 (s, 3 H) 1.27 (d, J=6.03 Hz, 3 H) 1.31 (s, 3 H) 1.51 - 1.71 (m, 5 H) 1.74 - 1.83 (m, 1 H) 1.84 - 1.92 (m, 1 H) 2.17 - 2.29 (m, 4 H) 2.26 (s, 6 H) 2.34 (s, 3 H) 2.34 - 2.38 (m, 1 H) 2.39 - 2.47 (m, 1 H) 2.48 - 2.56 (m, 1 H) 2.75 - 2.82 (m, 1 H) 2.87 - 2.94 (m, 1 H) 3.00 (t, J=7.82 Hz, 1 H) 3.19 (dd, J=10.15, 7.40 Hz, 1 H) 3.23 (s, 3 H) 3.26 - 3.38 (m, 1 H) 3.31 (s, 3 H) 3.40 - 3.52 (m, 2 H) 3.58 - 3.67 (m, 1 H) 3.69 (d, J=7.68 Hz, 1 H) 3.97 - 4.11 (m, 2 H) 4.40 (d, J=7.40 Hz, 1 H) 4.78 - 4.86 (m, 1 H) 4.89 (d, J=4.39 Hz, 1 H) 7.41 (br. s., 1 H) 7.88 (dd, J=5.21, 2.19 Hz, 1 H) 9.29 - 9.35 (m, 1 H) 9.55 (s, 1 H)
576		891.7	(500 MHz):0.72 - 0.85 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.14 (d, J=7.40 Hz, 3 H) 1.20 - 1.24 (m, 6 H) 1.29 - 1.34 (m, 6 H) 1.52 (dd, J=15.22, 4.80 Hz, 1 H) 1.58 - 1.72 (m, 4 H) 1.78 - 1.93 (m, 2 H) 2.15 - 2.20 (m, 1 H) 2.22 - 2.35 (m, 4 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.40 - 2.51 (m, 2 H) 2.79 - 2.85 (m, 1 H) 2.95 (d, J=14.81 Hz, 1 H) 2.98 - 3.04 (m, 1 H) 3.20 (s, 3 H) 3.21 - 3.26 (m, 1 H) 3.30 (s, 3 H) 3.41 - 3.54 (m, 4 H) 3.69 (d, J=7.68 Hz, 1 H) 4.01 - 4.10 (m, 1 H) 4.11 - 4.21 (m, 1 H) 4.40 (d, J=7.40 Hz, 1 H) 4.67 - 4.81 (m, 1 H) 4.91 (d, J=4.39 Hz, 1 H) 6.46 - 6.57 (m, 1 H) 7.16 - 7.23 (m, 2 H) 7.36 - 7.41 (m, 1 H) 7.81 - 7.87 (m, 1 H) 8.00 - 8.11 (m, 1 H) 9.72 (br. s., 1 H)
577		892.7	(500 MHz): 0.75-0.85 (m, 6 H) 1.06 (d, J=7.40 Hz, 3 H) 1.08 - 1.14 (m, 1 H) 1.13 (d, J=7.40 Hz, 3 H) 1.15 - 1.26 (m, 1 H) 1.19 - 1.24 (m, 6 H) 1.29 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.51 (dd, J=15.08, 4.66 Hz, 1 H) 1.57 - 1.71 (m, 4 H) 1.78 - 1.94 (m, 2 H) 2.07 - 2.18 (m, 1 H) 2.23 - 2.37 (m, 4 H) 2.29 (s, 6 H) 2.32 (s, 3 H) 2.38 - 2.44 (m, 1 H) 2.44 - 2.53 (m, 1 H) 2.77 - 2.85 (m, 1 H) 2.87 - 2.95 (m, 1 H) 3.00 (t, J=9.19 Hz, 1 H) 3.16 - 3.26 (m, 1 H) 3.22 (s, 3 H) 3.29 (s, 3 H) 3.39 - 3.57 (m, 4 H) 3.71 (d, J=7.95 Hz, 1 H) 3.98 - 4.10 (m, 1 H) 4.12 - 4.21 (m, 1 H) 4.40 (d, J=6.86 Hz, 1 H) 4.72 - 4.82 (m, 1 H) 4.92 (d, J=4.66 Hz, 1 H) 7.20 - 7.28 (m, 1 H) 7.32 - 7.40 (m, 2 H) 7.46 (d, J=8.23 Hz, 1 H) 8.37 (d, J=8.23 Hz, 1 H) 11.30 (br. s., 1 H)
578		903.7	(500 MHz):0.77 - 0.84 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.09 - 1.14 (m, 1 H) 1.16 (d, J=7.68 Hz, 3 H) 1.19 - 1.25 (m, 1 H) 1.19 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.60 - 1.77 (m, 4 H) 1.80 - 1.95 (m, 2 H) 2.13 - 2.21 (m, 1 H) 2.22 - 2.31 (m, 3 H) 2.28 (s, 6 H) 2.32 - 2.36 (m, 1 H) 2.36 (s, 3 H) 2.39 - 2.51 (m, 2 H) 2.74 - 2.84 (m, 1 H) 2.94 (d, J=14.54 Hz, 1 H) 3.00 (t, J=9.46 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.43 (m, 1 H) 3.43 - 3.59 (m, 3 H) 3.69 (d, J=8.23 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.11 - 4.19 (m, 1 H) 4.38 (d, J=7.40 Hz, 1 H) 4.72 - 4.83 (m, 1 H) 4.92 (d, J=4.39 Hz, 1 H) 7.62 - 7.74 (m, 2 H) 7.79 (d, J=5.49 Hz, 1 H) 7.84 (d, J=7.68 Hz, 1 H) 8.22 - 8.29 (m, 1 H) 8.46 (d, J=5.48 Hz, 1 H) 9.58 (d, J=8.78 Hz, 1 H)

[1203] 

[Table 15-4]

579		903.7	(500 MHz):0.78 - 0.86 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.10 - 1.24 (m, 2 H) 1.16 (d, J=7.40 Hz, 3 H) 1.20 - 1.22 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.03 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.36, 4.94 Hz, 1 H) 1.60 - 1.66 (m, 1 H) 1.67 - 1.87 (m, 4 H) 1.90 - 1.98 (m, 1 H) 2.13 - 2.20 (m, 1 H) 2.20 - 2.38 (m, 4 H) 2.28 (s, 6 H) 2.36 (s, 3 H) 2.39 - 2.52 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.90 - 2.97 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.20 (dd, J=10.15, 7.40 Hz, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.43 - 3.51 (m, 1 H) 3.56 - 3.65 (m, 2 H) 3.69 (d, J=8.23 Hz, 1 H) 3.96 - 4.09 (m, 1 H) 4.11 - 4.19 (m, 1 H) 4.38 (d, J=7.40 Hz, 1 H) 4.71 - 4.84 (m, 1 H) 4.93 (d, J=4.39 Hz, 1 H) 7.49 (dd, J=8.23, 4.39 Hz, 1 H) 7.63 - 7.70 (m, 1 H) 7.95 (dd, J=8.09, 1.51 Hz, 1 H) 8.27 (dd, J=8.36, 1.78 Hz, 1 H) 8.85 (dd, J=7.27, 1.51 Hz, 1 H) 8.92 (dd, J=4.11, 1.92 Hz, 1 H) 11.26 - 11.34 (m, 1 H)
580		904.7	(500 MHz):0.77 - 0.87 (m, 6 H) 1.07 (d, J=7.40 Hz, 3 H) 1.11 (d, J=7.40 Hz, 3 H) 1.12 - 1.16 (m, 1 H) 1.18 - 1.24 (m, 1 H) 1.19 - 1.22 (m, 3 H) 1.22 (s, 3 H) 1.27,(d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.22, 4.80 Hz, 1 H) 1.60 - 1.77 (m, 4 H) 1.80 - 1.95 (m, 2 H) 2.15 - 2.29 (m, 4 H) 2.27 (s, 6 H) 2.30 - 2.35 (m, 1 H) 2.36 (s, 3 H) 2.39 - 2.52 (m, 2 H) 2.71 - 2.80 (m, 1 H) 2.90 - 2.97 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.15 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.30 (s, 3 H) 3.32 - 3.40 (m, 1 H) 3.41 - 3.50 (m, 1 H) 3.53 - 3.65 (m, 2 H) 3.68 (d, J=7.95 Hz, 1 H) 3.98 - 4.07 (m, 1 H) 4.06 - 4.13 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.75 - 4.85 (m, 1 H) 4.88 (d, J=4.66 Hz, 1 H) 6.85 - 7.03 (m, 1 H) 7.49 (d, J=4.39 Hz, 1 H) 7.52 (dd, J=8.50, 4.11 Hz, 1 H) 8.68 (dd, J=8.50, 1.92 Hz, 1 H) 9.01 (d, J=4.39 Hz, 1 H) 9.09 (dd, J=4.11, 1.92 Hz, 1 H)
581		904.6	(500 MHz):0.78 - 0.86 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.12 - 1.23 (m, 2 H) 1.16 (d, J=7.40 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 5.07 Hz, 1 H) 1.59 - 1.77 (m, 4 H) 1.80 - 1.93 (m, 2 H) 2.16 - 2.21 (m, 1 H) 2.21 - 2.31 (m, 3 H) 2.28 (s, 6 H) 2.32 - 2.37 (m, 1 H) 2.36 (s, 3 H) 2.39 - 2.50 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.91 - 2.96 (m, 1 H) 3.00 (t, J=9.32 Hz, 1 H) 3.20 (dd, J=10.42, 7.40 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.42 - 3.59 (m, 3 H) 3.69 (d, J=7.95 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.10 - 4.20 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.74 - 4.84 (m, 1 H) 4.92 (d, J=4.66 Hz, 1 H) 7.58 (dd, J=8.78, 4.11 Hz, 1 H) 8.06 (dd, J=5.62, 0.69 Hz, 1 H) 8.29 - 8.36 (m, 1 H) 8.68 (d, J=5.76 Hz, 1 H) 9.09 (dd, J=4.11, 1.65 Hz, 1 H) 9.94 - 10.03 (m, 1 H)
582		853.6	(500 MHz):0.79 - 0.86 (m, 6 H) 1.09 (d, J=7.65 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.16 (d, J=7.65 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.88 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.29, 4.59 Hz, 1 H) 1.57 - 1.73 (m, 4 H) 1.78 - 1.92 (m, 2 H) 2.13 - 2.19 (m, 1 H) 2.22 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.33 - 2.38 (m, 1 H) 2.36 (s, 3 H) 2.40 - 2.51 (m, 2 H) 2.77 - 2.84 (m, 1 H) 2.90 - 2.96 (m, 1 H) 3.00 (t, J=9.56 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.42 - 3.52 (m, 3 H) 3.70 (d, J=7.65 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.12 - 4.19 (m, 1 H) 4.38 (d, J=7.65 Hz, 1 H) 4.70 - 4.82 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 7.39 - 7.44 (m, 1 H) 7.81 - 7.86 (m, 1 H) 8.03 - 8.10 (m, 1 H) 8.18 (d, J=7.65 Hz, 1 H) 8.55 (d, J=4.59 Hz, 1 H)

[1204] 

[Table 15-5]

583		853.7	(500 MHz):0.79 - 0.88 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.11 - 1.26 (m, 2 H) 1.15 (d, J=7.13 Hz, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.22, 4.80 Hz, 1 H) 1.57 - 1.91 (m, 6 H) 2.16 - 2.31 (m, 4 H) 2.27 (s, 6 H) 2.33 - 2.40 (m, 1 H) 2.36 (s, 3 H) 2.40 - 2.54 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.88 - 2.95 (m, 1 H) 3.01 (t, J=9.60 Hz, 1 H) 3.20 (dd, J=10.15, 7.13 Hz, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.33 - 3.40 (m, 1 H) 3.40 - 3.52 (m, 2 H) 3.53 - 3.63 (m, 1 H) 3.70 (d, J=7.95 Hz, 1 H) 3.99 - 4.07 (m, 1 H) 4.07 - 4.14 (m, 1 H) 4.40 (d, J=7.13 Hz, 1 H) 4.75 - 4.87 (m, 1 H) 4.91 (d, J=4.66 Hz, 1 H) 6.66 (br. s., 1 H) 7.63 (d, J=5.76 Hz, 2 H) 8.69 - 8.75 (m, 2 H)
584		854.6	(500 MHz):0.79 - 0.90 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.12 - 1.26 (m, 2 H) 1.16 (d, J=7.26 Hz, 3 H) 1.21 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.27 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.55 (dd, J=15.29, 4.97 Hz, 2 H) 1.59 - 1.72 (m, 4 H) 1.73 - 1.83 (m, 1 H) 1.84 - 1.96 (m, 1 H) 2.18 - 2.31 (m, 4 H) 2.27 (s, 6 H) 2.33 - 2.38 (m, 1 H) 2.35 (s, 3 H) 2.41 - 2.53 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.88 - 2.95 (m, 1 H) 3.00 (t, J=9.37 Hz, 1 H) 3.20 (dd, J=10.32, 7.26 Hz, 1 H) 3.23 (s, 3 H) 3.28 - 3.39 (m, 1 H) 3.31 (s, 3 H) 3.41 - 3.51 (m, 2 H) 3.54 - 3.64 (m, 1 H) 3.70 (d, J=7.64 Hz, 1 H) 3.98 - 4.09 (m, 2 H) 4.40 (d, J=7.26 Hz, 1 H) 4.79 - 4.87 (m, 1 H) 4.89 (d, J=4.59 Hz, 1 H) 9.13 (s, 2 H) 9.29 (s, 1 H)
585		890.6	(500 MHz):0.77 - 0.88 (m, 6 H) 1.09 (d, J=7.64 Hz, 3 H) 1.11 - 1.18 (m, 1 H) 1.16 (d, J=7.26 Hz, 3 H) 1.19 - 1.26 (m, 1 H) 1.20 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.29, 4.59 Hz, 1 H) 1.56 - 1.69 (m, 4 H) 1.72 - 1.90 (m, 2 H) 2.13 - 2.22 (m, 1 H) 2.22 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.32 - 2.38 (m, 1 H) 2.36 (s, 3 H) 2.41 - 2.52 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.89 - 2.96 (m, 1 H) 3.00 (t, J=8.60 Hz, 1 H) 3.20 (dd, J=10.32, 7.26 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.54 (m, 6 H) 3.70 (d, J=8.03 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.72 - 4.83 (m, 1 H) 4.92 (d, J=4.20 Hz, 1 H) 6.16 (br. s., 1 H) 6.91 - 6.96 (m, 1 H) 7.22 - 7.27 (m, 1 H) 7.33 (t, J=7.64 Hz, 1 H) 7.47 (d, J=7.26 Hz, 1 H) 7.88 (d, J=7.65 Hz, 1 H)
586		892.7	(500 MHz):0.76 - 0.87 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.10 - 1.26 (m, 2 H) 1.17 (d, J=7.26 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.29, 4.97 Hz, 1 H) 1.56 - 1.75 (m, 4 H) 1.78 - 1.90 (m, 2 H) 2.13 - 2.21 (m, 1 H) 2.21 - 2.31 (m, 3 H) 2.27 (s, 6 H) 2.31 - 2.38 (m, 1 H) 2.36 (s, 3 H) 2.40 - 2.51 (m, 2 H) 2.75 - 2.84 (m, 1 H) 2.89 - 2.95 (m, 1 H) 3.00 (t, J=9.37 Hz, 1 H) 3.20 (dd, J=10.32, 7.26 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.42 - 3.57 (m, 3 H) 3.70 (d, J=8.03 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.09 - 4.19 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.73 - 4.83 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 6.65 - 6.78 (m, 1 H) 7.28 (t, J=7.45 Hz, 1 H) 7.37 - 7.42 (m, 1 H) 7.45 (s, 1 H) 7.50 (d, J=8.41 Hz, 1 H) 7.66 (d, J=7.64 Hz, 1 H)

[1205] 

[Table 15-6]

587		908.6	(500 MHz):0.79 - 0.91 (m, 6 H) 1.09 (d, J=7.65 Hz, 3 H) 1.13 - 1.19 (m, 1 H) 1.15 (d, J=7.65 Hz, 3 H) 1.19 - 1.27 (m, 1 H) 1.21 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.29, 5.35 Hz, 1 H) 1.59 - 1.76 (m, 4 H) 1.80 - 1.94 (m, 2 H) 2.16 - 2.32 (m, 4 H) 2.28 (s, 6 H) 2.32 - 2.39 (m, 1 H) 2.37 (s, 3 H) 2.41 - 2.51 (m, 2 H) 2.70 - 2.84 (m, 1 H) 2.90 - 2.97 (m, 1 H) 3.01 (t, J=9.56 Hz, 1 H) 3.20 (dd, J=9.94, 7.65 Hz, 1 H) 3.24 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.43 - 3.51 (m, 2 H) 3.51 - 3.61 (m, 1 H) 3.70 (d, J=7.65 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.40 (d, J=6.88 Hz, 1 H) 4.72 - 4.86 (m, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 6.30 (br. s., 1 H) 7.34 - 7.42 (m, 1 H) 7.41 - 7.47 (m, 1 H) 7.85 (d, J=8.41 Hz, 1 H) 7.87 (s, 1 H) 8.38 (d, J=7.65 Hz, 1 H)
588		891.7	(500 MHz):0.76 - 0.88 (m, 6 H) 1.08 (d, J=7.26 Hz, 3 H) 1.10 - 1.18 (m, 1 H) 1.15 (d, J=7.26 Hz, 3 H) 1.19 - 1.26 (m, 1 H) 1.20 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.29, 4.97 Hz, 1 H) 1.60 - 1.78 (m, 4 H) 1.80 - 1.97 (m, 2 H) 2.12 - 2.21 (m, 1 H) 2.21 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.31 - 2.38 (m, 1 H) 2.36 (s, 3 H) 2.40 - 2.54 (m, 2 H) 2.77 - 2.83 (m, 1 H) 2.90 - 2.97 (m, 1 H) 3.00 (t, J=9.75 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.36 - 3.42 (m, 1 H) 3.43 - 3.49 (m, 1 H) 3.50 - 3.60 (m, 2 H) 3.70 (d, J=8.03 Hz, 1 H) 4.00 - 4.11 (m, 1 H) 4.11 - 4.20 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.72 - 4.83 (m, 1 H) 4.92 (d, J=4.20 Hz, 1 H) 6.25 - 6.37 (m, 1 H) 6.89 - 6.93 (m, 1 H) 7.21 (t, J=7.84 Hz, 1 H) 7.28 - 7.35 (m, 1 H) 7.49 (dd, J=11.85, 7.64 Hz, 2 H) 8.63 - 8.74 (m, 1 H)
589		891.7	(500 MHz):0.79 - 0.88 (m, 6 H) 1.10 (d, J=6.88 Hz, 3 H) 1.13 - 1.19 (m, 1 H) 1.16 (d, J=7.65 Hz, 3 H) 1.20 - 1.27 (m, 1 H) 1.21 - 1.23 (m, 3 H) 1.23 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.54 (dd, J=15.29, 4.59 Hz, 1 H) 1.58 - 1.74 (m, 4 H) 1.78 - 1.91 (m, 2 H) 2.14 - 2.22 (m, 1 H) 2.22 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.32 - 2.39 (m, 1 H) 2.36 (s, 3 H) 2.42 - 2.53 (m, 2 H) 2.74 - 2.85 (m, 1 H) 2.87 - 2.96 (m, 1 H) 3.01 (t, J=9.94 Hz, 1 H) 3.21 (dd, J=10.32, 7.26 Hz, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.43 - 3.52 (m, 2 H) 3.54 - 3.63 (m, 1 H) 3.71 (d, J=7.65 Hz, 1 H) 3.98 - 4.08 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.40 (d, J=7.65 Hz, 1 H) 4.74 - 4.87 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 6.48 - 6.65 (m, 2 H) 7.10 (t, J=7.65 Hz, 1 H) 7.29 - 7.34 (m, 1 H) 7.38 (d, J=6.88 Hz, 1 H) 7.79 (d, J=7.65 Hz, 1 H) 10.28 - 10.38 (m, 1 H)
590		842.6	(500 MHz):0.75 - 0.85 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.11 - 1.18 (m, 1 H) 1.16 (d, J=7.26 Hz, 3 H) 1.19 - 1.25 (m, 1 H) 1.21 (d, J=6.12 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.67 (m, 5 H) 1.71 - 1.78 (m, 1 H) 1.79 - 1.89 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.22 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.32 - 2.37 (m, 1 H) 2.35 (s, 3 H) 2.40 - 2.50 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.89 - 2.95 (m, 1 H) 3.00 (t, J=9.75 Hz, 1 H) 3.20 (dd, J=10.32, 7.26 Hz, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.50 (m, 4 H) 3.69 (d, J=8.03 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.38 (d, J=7.26 Hz, 1 H) 4.64 - 4.81 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 6.38 - 6.45 (m, 1 H) 6.48 (dd, J=3.44, 1.53 Hz, 1 H) 7.07 - 7.11 (m, 1 H) 7.39 - 7.44 (m, 1 H)

[1206] 

[Table 15-7]

591		841.6	(500 MHz):0.80 - 0.87 (m, 6 H) 1.10 (d, J=7.26 Hz, 3 H) 1.13 - 1.18 (m, 1 H) 1.16 (d, J=7.64 Hz, 3 H) 1.20 - 1.26 (m, 1 H) 1.22 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.51 - 1.73 (m, 5 H) 1.75 - 1.83 (m, 1 H) 1.83 - 1.91 (m, 1 H) 2.13 - 2.21 (m, 1 H) 2.23 - 2.31 (m, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.35 - 2.40 (m, 1 H) 2.41 - 2.52 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.88 - 2.95 (m, 1 H) 3.01 (t, J=9.75 Hz, 1 H) 3.17 - 3.22 (m, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.43 (m, 2 H) 3.43 - 3.52 (m, 2 H) 3.70 (d, J=8.03 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.40 (d, J=6.88 Hz, 1 H) 4.72 - 4.85 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 6.01 - 6.16 (m, 1 H) 6.19 - 6.24 (m, 1 H) 6.54 - 6.60 (m, 1 H) 6.87 - 6.94 (m, 1 H) 9.38 (br. s., 1 H)
592		858.6	(500 MHz): 0.79-0.88 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.09 - 1.18 (m, 1 H) 1.16 (d, J=7.40 Hz, 3 H) 1.18 - 1.25 (m, 1 H) 1.21 (d, J=6.03 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.03 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.57 - 1.66 (m, 4 H) 1.73 - 1.81 (m, 1 H) 1.82 - 1.92 (m, 1 H) 2.12 - 2.22 (m, 1 H) 2.22 - 2.31 (m, 3 H) 2.27 (s, 6 H) 2.35 (s, 3 H) 2.35 - 2.39 (m, 1 H) 2.40 - 2.50 (m, 2 H) 2.73 - 2.83 (m, 1 H) 2.91 (d, J=14.26 Hz, 1 H) 3.00 (t, J=9.46 Hz, 1 H) 3.20 (dd, J=10.28, 7.27 Hz, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.43 (m, 2 H) 3.43 - 3.54 (m, 2 H) 3.70 (d, J=7.95 Hz, 1 H) 3.98 - 4.08 (m, 1 H) 4.09 - 4.17 (m, 1 H) 4.39 (d, J=7.40 Hz, 1 H) 4.72 - 4.85 (m, 1 H) 4.91 (d, J=4.39 Hz, 1 H) 6.24 (br. s., 1 H) 7.05 (dd, J=4.94, 3.84 Hz, 1 H) 7.44 (dd, J=4.94, 1.10 Hz, 1 H) 7.50 (dd, J=3.70, 0.96 Hz, 1 H)
593		842.6	(500 MHz):0.75 - 0.86 (m, 6 H) 1.08 (d, J=7.13 Hz, 3 H) 1.12 - 1.17 (m, 1 H) 1.14 (d, J=7.40 Hz, 3 H) 1.20 - 1.23 (m, 3 H) 1.20 - 1.26 (m, 1 H) 1.22 (s, 3 H) 1.29 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.22, 5.07 Hz, 1 H) 1.57 - 1.69 (m, 4 H) 1.73 - 1.90 (m, 2 H) 2.13 - 2.28 (m, 3 H) 2.29 (s, 6 H) 2.31 - 2.35 (m, 1 H) 2.36 (s, 3 H) 2.41 - 2.46 (m, 1 H) 2.47 - 2.53 (m, 1 H) 2.79 - 2.84 (m, 1 H) 2.95 (d, J=13.71 Hz, 1 H) 3.01 (d, J=9.05 Hz, 1 H) 3.20 (s, 3 H) 3.24 (dd, J=10.15, 7.40 Hz, 1 H) 3.30 (s, 3 H) 3.35 - 3.51 (m, 4 H) 3.68 (d, J=7.40 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.11 - 4.19 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.67 - 4.83 (m, 1 H) 4.90 (d, J=4.66 Hz, 1 H) 6.71 - 6.77 (m, 1 H) 8.02 (s, 2 H)
594		860.6	(500 MHz):0.78 - 0.84 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.10 - 1.14 (m, 1 H) 1.16 (d, J=7.40 Hz, 3 H) 1.19 - 1.22 (m, 1 H) 1.21 (d, J=6.03 Hz, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.56 - 1.66 (m, 3 H) 1.67 - 1.80 (m, 2 H) 1.81 - 1.93 (m, 1 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.34 (m, 3 H) 2.27 (s, 6 H) 2.34 - 2.38 (m, 1 H) 2.35 (s, 3 H) 2.40 - 2.49 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.93 (d, J=15.63 Hz, 1 H) 3.00 (t, J=9.46 Hz, 1 H) 3.13 - 3.20 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.42 - 3.49 (m, 1 H) 3.50 - 3.59 (m, 2 H) 3.69 (d, J=7.95 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.70 - 4.84 (m, 1 H) 4.92 (d, J=4.39 Hz, 1 H) 7.58 - 7.64 (m, 1 H) 9.21 (s, 1 H)

[1207] 

[Table 15-8]

595		843.7	(500 MHz):0.77 - 0.85 (m, 6 H) 1.07 - 1.10 (m, 3 H) 1.10 - 1.17 (m, 1 H) 1.13 - 1.17 (m, 3 H) 1.18 - 1.25 (m, 1 H) 1.19 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.47 - 1.71 (m, 5 H) 1.73 - 1.89 (m, 2 H) 2.09 - 2.20 (m, 1 H) 2.20 - 2.32 (m, 2 H) 2.28 (s, 6 H) 2.31 - 2.40 (m, 4 H) 2.41 - 2.52 (m, 2 H) 2.63 - 2.84 (m, 3 H) 2.87 - 2.95 (m, 1 H) 3.00 (d, J=9.32 Hz, 1 H) 3.17 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.50 (m, 2 H) 3.69 (d, J=8.23 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.66 - 4.79 (m, 1 H) 4.89 - 4.95 (m, 1 H)
596		842.6	(500 MHz):0.73 - 0.89 (m, 6 H) 1.07 (d, J=7.40 Hz, 3 H) 1.10 - 1.18 (m, 1 H) 1.15 (d, J=7.40 Hz, 3 H) 1.18 - 1.25 (m, 1 H) 1.20 - 1.23 (m, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.56 - 1.68 (m, 4 H) 1.74 - 1.90 (m, 2 H) 2.10 - 2.18 (m, 1 H) 2.19 - 2.29 (m, 3 H) 2.28 (s, 6 H) 2.34 (s, 3 H) 2.34 - 2.37 (m, 1 H) 2.38 - 2.44 (m, 1 H) 2.44 - 2.52 (m, 1 H) 2.74 - 2.84 (m, 1 H) 2.91 (d, J=13.44 Hz, 1 H) 3.00 (t, J=9.19 Hz, 1 H) 3.14 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.52 (m, 4 H) 3.69 (d, J=7.95 Hz, 1 H) 4.00 - 4.08 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.38 (d, J=7.40 Hz, 1 H) 4.70 - 4.79 (m, 1 H) 4.91 (d, J=4.66 Hz, 1 H) 7.19 (br. s., 1 H) 7.57 (s, 1 H) 7.60 (s, 1 H) 10.92 (br. s., 1 H)
597		843.6	(500 MHz):0.77 - 0.86 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.12 - 1.17 (m, 1 H) 1.17 (d, J=7.26 Hz, 3 H) 1.19 - 1.26 (m, 1 H) 1.22 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.50 - 1.75 (m, 5 H) 1.77 - 1.91 (m, 2 H) 2.14 - 2.23 (m, 1 H) 2.22 - 2.33 (m, 3 H) 2.29 (s, 6 H) 2.33 - 2.39 (m, 1 H) 2.36 (s, 3 H) 2.41 - 2.55 (m, 2 H) 2.77 - 2.85 (m, 1 H) 2.94 (d, J=15.67 Hz, 1 H) 3.01 (t, J=8.98 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.42 (m, 1 H) 3.42 - 3.54 (m, 3 H) 3.70 (d, J=8.03 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.73 - 4.83 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 6.63 - 6.77 (m, 1 H) 6.90 (d, J=1.15 Hz, 1 H) 8.27 - 8.37 (m, 1 H)
598		844.5	(500 MHz):0.80 - 0.92 (m, 6 H) 1.11 (d, J=6.88 Hz, 3 H) 1.18 (d, J=6.88 Hz, 3 H) 1.17 - 1.29 (m, 2 H) 1.21 - 1.24 (m, 3 H) 1.25 (s, 3 H) 1.29 (d, J=6.50 Hz, 3 H) 1.34 (s, 3 H) 1.51 - 1.81 (m, 6 H) 1.93 - 2.16 (m, 2 H) 2.30 - 2.42 (m, 12 H) 2.51 - 2.61 (m, 2 H) 2.79 - 2.88 (m, 2 H) 3.01 (d, J=9.56 Hz, 1 H) 3.21 - 3.27 (m, 1 H) 3.27 - 3.33 (m, 6 H) 3.33 - 3.43 (m, 2 H) 3.44 - 3.55 (m, 2 H) 3.72 - 3.75 (m, 1 H) 3.98 - 4.11 (m, 2 H) 4.36 - 4.41 (m, 1 H) 4.80 - 5.00 (m, 2 H)

[1208] 

[Table 15-9]

599		859.6	(500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.11 - 1.16 (m, 1 H) 1.16 (d, J=7.64 Hz, 3 H) 1.19 - 1.26 (m, 1 H) 1.20 - 1.24 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.10, 4.78 Hz, 1 H) 1.56 - 1.75 (m, 4 H) 1.77 - 1.88 (m, 2 H) 2.10 - 2.20 (m, 1 H) 2.21 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.34 - 2.37 (m, 1 H) 2.35 (s, 3 H) 2.40 - 2.51 (m, 2 H) 2.75 - 2.85 (m, 1 H) 2.93 (d, J=13.38 Hz, 1 H) 3.00 (t, J=9.75 Hz, 1 H) 3.17 - 3.23 (m, 1 H) 3.22 - 3.23 (m, 3 H) 3.32 (s, 3 H) 3.34 - 3.52 (m, 4 H) 3.70 (d, J=8.03 Hz, 1 H) 4.01 - 4.09 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.38 (d, J=7.26 Hz, 1 H) 4.67 - 4.80 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 7.38 - 7.46 (m, 1 H) 8.15 (d, J=1.91 Hz, 1 H) 8.74 (d, J=2.29 Hz, 1 H)
600		841.6	(500 MHz):0.73 - 0.91 (m, 6 H) 1.08 (d, J=7.26 Hz, 3 H) 1.12 - 1.19 (m, 1 H) 1.15 (d, J=7.26 Hz, 3 H) 1.17 - 1.26 (m, 1 H) 1.19 - 1.25 (m, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.29, 4.59 Hz, 1 H) 1.56 - 1.68 (m, 4 H) 1.76 - 1.89 (m, 2 H) 2.11 - 2.21 (m, 1 H) 2.22 - 2.30 (m, 3 H) 2.28 (s, 6 H) 2.35 (s, 3 H) 2.33 - 2.38 (m, 1 H) 2.39 - 2.51 (m, 2 H) 2.76 - 2.83 (m, 1 H) 2.91 (d, J=13.76 Hz, 1 H) 3.00 (t, J=9.36 Hz, 1 H) 3.18 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.34 - 3.52 (m, 4 H) 3.70 (d, J=8.03 Hz, 1 H) 4.00 - 4.09 (m, 1 H) 4.11 - 4.19 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.70 - 4.81 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 6.09 (br. s., 1 H) 6.41 - 6.46 (m, 1 H) 6.70 - 6.76 (m, 1 H) 7.33 - 7.39 (m, 1 H) 9.12 (br. s., 1 H)
601		859.6	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.10 - 1.17 (m, 1 H) 1.16 (d, J=7.64 Hz, 3 H) 1.18 - 1.26 (m, 1 H) 1.21 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.53 (dd, J=15.10, 4.78 Hz, 1 H) 1.56 - 1.78 (m, 4 H) 1.79 - 1.89 (m, 2 H) 2.12 - 2.20 (m, 1 H) 2.22 - 2.32 (m, 3 H) 2.28 (s, 6 H) 2.33 - 2.38 (m, 1 H) 2.35 (s, 3 H) 2.40 - 2.50 (m, 2 H) 2.75 - 2.84 (m, 1 H) 2.93 (d, J=14.53 Hz, 1 H) 3.00 (t, J=9.56 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.42 - 3.50 (m, 3 H) 3.69 (d, J=8.03 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.10 - 4.17 (m, 1 H) 4.38 (d, J=7.26 Hz, 1 H) 4.70 - 4.79 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 7.29 - 7.36 (m, 1 H) 7.55 (d, J=3.06 Hz, 1 H) 7.84 (d, J=3.06 Hz, 1 H)
602		812.4	(600 MHz):0.75 - 0.84 (m, 6 H) 1.06 - 1.26 (m, 11 H) 1.10 (d, J=7.34 Hz, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.36, 4.81 Hz, 1 H) 1.61 - 1.67 (m, 1 H) 1.77 - 1.86 (m, 1 H) 2.02 - 2.49 (m, 9 H) 2.27 (s, 6 H) 2.34 (s, 3 H) 2.81 - 2.89 (m, 1 H) 2.94 - 3.03 (m, 2 H) 3.19 (dd, J=10.09, 7.34 Hz, 1 H) 3.21 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.41 (m, 1 H) 3.42 - 3.48 (m, 1 H) 3.69 (d, J=7.79 Hz, 1 H) 3.86 - 3.96 (m, 2 H) 4.02 - 4.08 (m, 1 H) 4.14 - 4.20 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.75 - 4.78 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 6.14 (dd, J=13.30, 1.38 Hz, 1 H) 6.54 (d, J=9.17 Hz, 1 H) 7.20 (d, J=6.42 Hz, 1 H) 7.29 - 7.32 (m, 1 H)

[1209] 

[Table 15-10]

603		826.4	(600 MHz):0.77 - 0.85 (m, 6 H) 1.08 (d, J=7.34 Hz, 3 H) 1.07 - 1.25 (m, 8 H) 1.14 (d, J=7.34 Hz, 3 H) 1.27 (d, J=5.96 Hz, 3 H) 1.31 (s, 3 H) 1.50 - 1.86 (m, 7 H) 2.08 - 2.49 (m, 7 H) 2.28 (s, 6 H) 2.33 (s, 3 H) 2.75 - 2.81 (m, 1 H) 2.87 - 2.94 (m, 1 H) 3.00 (t, J=9.86 Hz, 1 H) 3.16 - 3.49 (m, 3 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.69 (d, J=7.79 Hz, 1 H) 3.86 - 3.97 (m, 2 H) 4.01 - 4.07 (m, 1 H) 4.09 - 4.15 (m, 1 H) 4.38 (d, J=7.34 Hz, 1 H) 4.71 - 4.78 (m, 1 H) 4.91 (d, J=4.59 Hz, 1 H) 6.10 - 6.16 (m, 1 H) 6.54 (d, J=9.17 Hz, 1 H) 7.21 - 7.23 (m, 1 H) 7.27 - 7.31 (m, 1 H)
604		804.5	(500 MHz): 0.87 (d, J=7.26 Hz, 3 H) 0.93 (d, J=6.50 Hz, 3 H) 1.08 (d, J=7.64 Hz, 3 H) 1.11 (d, J=7.26 Hz, 3 H) 1.16 - 1.29 (m, 2 H) 1.21 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.26 (d, J=6.12 Hz, 3 H) 1.29 (s, 3 H) 1.48 - 1.56 (m, 1 H) 1.57 - 1.64 (m, 1 H) 1.87 - 1.96 (m, 1 H) 2.18 - 2.22 (m, 1 H) 2.21 - 2.41 (m, 13 H) 2.42 - 2.52 (m, 1 H) 2.54 - 2.62 (m, 1 H) 2.72 - 2.80 (m, 1 H) 2.91 - 3.03 (m, 2 H) 3.18 - 3.29 (m, 2 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.43 - 3.52 (m, 1 H) 3.59 - 3.66 (m, 1 H) 3.70 (d, J=7.64 Hz, 1 H) 3.80 - 3.92 (m, 1 H) 3.95 - 4.07 (m, 2 H) 4.42 (d, J=6.88 Hz, 1 H) 4.63 (q, J=15.80 Hz, 2 H) 4.79 - 4.86 (m, 1 H) 5.12 - 5.21 (m, 1 H)
605		799.5	(500 MHz):0.79 (d, J=6.88 Hz, 3 H) 0.82 (d, J=6.50 Hz, 3 H) 0.90 (d, J=6.88 Hz, 3 H) 1.07 (d, J=7.64 Hz, 3 H) 1.08 - 1.30 (m, 8 H) 1.26 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.48 (dd, J=15.10, 4.78 Hz, 1 H) 1.64 (d, J=12.23 Hz, 1 H) 1.75 - 1.89 (m, 1 H) 2.19 - 2.50 (m, 7 H) 2.27 (s, 6 H) 2.39 (s, 3 H) 2.69 (m, 1 H) 2.97 (t, J=9.56 Hz, 1 H) 3.09 - 3.18 (m, 2 H) 3.18 (s, 3 H) 3.27 (s, 3 H) 3.27 - 3.34 (m, 1 H) 3.37 - 3.49 (m, 1 H) 3.66 (d, J=8.03 Hz, 1 H) 3.70 - 3.81 (m, 1 H) 3.93 - 4.05 (m, 1 H) 4.06 - 4.14 (m, 1 H) 4.34 (d, J=7.26 Hz, 1 H) 4.45 - 4.71 (m, 1 H) 4.81 (d, J=4.59 Hz, 1 H) 4.95 - 5.16 (m, 1 H) 6.22 - 6.32 (m, 1 H) 7.65 - 7.75 (m, 1 H) 8.49 - 8.66 (m, 1 H)
606		799.5	(500 MHz):0.79 - 0.89 (m, 6 H) 1.08 (d, J=7.64 Hz, 3 H) 1.10 - 1.15 (m, 1 H) 1.14 (d, J=7.64 Hz, 3 H) 1.19 - 1.26 (m, 7 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.49 - 1.56 (m, 1 H) 1.59 - 1.76 (m, 1 H) 1.79 - 1.90 (m, 1 H) 2.17 - 2.37 (m, 5 H) 2.30 (s, 6 H) 2.40 (s, 3 H) 2.44 - 2.55 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.95 - 3.07 (m, 2 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.52 (m, 2 H) 3.70 (d, J=8.03 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.44 - 4.60 (m, 2 H) 4.91 (d, J=4.59 Hz, 1 H) 5.07 - 5.19 (m, 1 H) 6.94 (t, J=4.78 Hz, 1 H) 8.50 (d, J=4.59 Hz, 2 H)

[1210] 

[Table 15-11]

607		849.5	(500 MHz):0.78 - 0.88 (m, 9 H) 1.07 (d, J=7.26 Hz, 3 H) 1.10 - 1.23 (m, 2 H) 1.16 (s, 3 H) 1.19 (d, J=6.12 Hz, 3 H) 1.24 (d, J=6.50 Hz, 3 H) 1.31 (s, 3 H) 1.40 (dd, J=15.10, 4.78 Hz, 1 H) 1.60 - 1.65 (m, 1 H) 1.78 - 1.87 (m, 1 H) 2.15 - 2.34 (m, 4 H) 2.27 (s, 6 H) 2.35 - 2.52 (m, 3 H) 2.44 (s, 3 H) 2.71 - 2.79 (m, 1 H) 2.94 (t, J=9.56 Hz, 1 H) 3.08 - 3.17 (m, 2 H) 3.18 (s, 3 H) 3.24 (s, 3 H) 3.30 - 3.37 (m, 1 H) 3.39 - 3.47 (m, 1 H) 3.65 (d, J=8.03 Hz, 1 H) 3.84 - 3.93 (m, 1 H) 3.95 - 4.02 (m, 1 H) 4.03 - 4.08 (m, 1 H) 4.34 (d, J=7.26 Hz, 1 H) 4.50 - 4.66 (m, 1 H) 4.75 (d, J=4.59 Hz, 1 H) 5.05 (br. s., 1 H) 7.45 - 7.52 (m, 1 H) 7.65 - 7.70 (m, 1 H) 7.71 - 7.76 (m, 1 H) 8.03 (s, 1 H) 8.27 (dd, J=8.03, 1.53 Hz, 1 H)
608		798.5	(500 MHz):0.79 - 0.87 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.13 (d, J=7.40 Hz, 3 H) 1.15 - 1.25 (m, 2 H) 1.20 - 1.22 (m, 3 H) 1.22 (s, 3 H) 1.27 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 1.52 (dd, J=15.08, 4.94 Hz, 1 H) 1.59 - 1.68 (m, 1 H) 1.81 - 1.89 (m, 1 H) 2.22 - 2.37 (m, 5 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.42 - 2.51 (m, 2 H) 2.72 - 2.83 (m, 1 H) 2.93 - 3.04 (m, 2 H) 3.14 - 3.23 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.43 (m, 1 H) 3.42 - 3.52 (m, 1 H) 3.69 (d, J=7.95 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.39 - 4.51 (m, 2 H) 4.91 (d, J=4.66 Hz, 1 H) 5.11 (br. s., 1 H) 6.65 - 6.71 (m, 1 H) 6.82 - 6.89 (m, 1 H) 7.49 - 7.58 (m, 1 H) 8.08 - 8.15 (m, 1 H)
609		848.6	(500 MHz):0.22 - 0.49 (m, 3 H) 0.86 (t, J=6.58 Hz, 6 H) 0.99 (d, J=7.40 Hz, 3 H) 1.11 - 1.25 (m, 2 H) 1.16 (s, 3 H) 1.19 (d, J=6.03 Hz, 3 H) 1.22 (d, J=6.31 Hz, 3 H) 1.30 (s, 3 H) 1.40 (dd, J=15.22, 3.98 Hz, 1 H) 1.60 - 1.67 (m, 1 H) 1.82 - 1.91 (m, 1 H) 2.14 - 2.30 (m, 4 H) 2.27 (s, 6 H) 2.33 - 2.61 (m, 4 H) 2.48 (s, 3 H) 2.93 (t, J=9.60 Hz, 1 H) 3.01 (d, J=14.54 Hz, 1 H) 3.17 (s, 3 H) 3.18 - 3.25 (m, 2 H) 3.22 (s, 3 H) 3.40 - 3.47 (m, 1 H) 3.63 (d, J=7.68 Hz, 1 H) 3.91 - 4.01 (m, 2 H) 4.34 (d, J=6.86 Hz, 1 H) 4.45 - 4.58 (m, 1 H) 4.59 - 4.67 (m, 1 H) 4.69 - 4.73 (m, 1 H) 5.17 - 5.28 (m, 1 H) 6.65 (d, J=9.60 Hz, 1 H) 7.20 (t, J=7.40 Hz, 1 H) 7.47 - 7.52 (m, 1 H) 7.54 - 7.59 (m, 1 H) 7.64 (d, J=9.32 Hz, 2 H)
610		845.6	(500 MHz):0.49 - 0.58 (m, 3 H) 0.84 (d, J=7.13 Hz, 3 H) 0.87 (d, J=6.58 Hz, 3 H) 1.03 (d, J=7.40 Hz, 3 H) 1.07 - 1.27 (m, 2 H) 1.18 (s, 3 H) 1.20 (d, J=6.31 Hz, 3 H) 1.24 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.43 (dd, J=15.22, 4.80 Hz, 1 H) 1.60 - 1.67 (m, 1 H) 1.81 - 1.88 (m, 1 H) 2.17 - 2.31 (m, 4 H) 2.27 (s, 6 H) 2.31 - 2.39 (m, 1 H) 2.39 - 2.59 (m, 3 H) 2.45 (s, 3 H) 2.95 (t, J=9.74 Hz, 1 H) 3.09 - 3.14 (m, 1 H) 3.15 - 3.21 (m, 1 H) 3.17 (s, 3 H) 3.21 - 3.32 (m, 1 H) 3.25 (s, 3 H) 3.37 - 3.50 (m, 1 H) 3.64 (d, J=7.95 Hz, 1 H) 3.89 - 3.95 (m, 1 H) 3.95 - 4.02 (m, 1 H) 4.27 (dd, J=14.54, 3.02 Hz, 1 H) 4.34 (d, J=7.40 Hz, 1 H) 4.43 - 4.53 (m, 1 H) 4.71 (d, J=4.11 Hz, 1 H) 4.97 - 5.12 (m, 1 H) 7.26 - 7.29 (m, 1 H) 7.31 - 7.36 (m, 1 H) 7.43 (d, J=8.23 Hz, 1 H) 7.60 (s, 1 H) 7.72 (d, J=7.68 Hz, 1 H)

[1211] 

[Table 15-12]

611		848.6	(500 MHz): 0.84 (d, J=6.88 Hz, 3 H) 0.87 (d, J=6.88 Hz, 3 H) 1.08 (d, J=6.88 Hz, 3 H) 1.10 - 1.25 (m, 2 H) 1.15 (d, J=6.88 Hz, 3 H) 1.21 - 1.24 (m, 6 H) 1.28 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.53 (dd, J=14.91, 4.97 Hz, 1 H) 1.62 - 1.69 (m, 1 H) 1.82 - 1.92 (m, 1 H) 2.22 - 2.40 (m, 5 H) 2.29 (s, 6 H) 2.42 (s, 3 H) 2.45 - 2.52 (m, 2 H) 2.76 - 2.87 (m, 1 H) 2.94 - 3.06 (m, 2 H) 3.16 - 3.24 (m, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.37 - 3.44 (m, 1 H) 3.45 - 3.52 (m, 1 H) 3.71 (d, J=7.65 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.39 (d, J=7.65 Hz, 1 H) 4.53 - 4.62 (m, 1 H) 4.70 (dd, J=11.09, 4.97 Hz, 1 H) 4.92 (d, J=5.35 Hz, 1 H) 5.12 - 5.25 (m, 1 H) 6.86 (d, J=9.17 Hz, 1 H) 7.37 (t, J=7.65 Hz, 1 H) 7.57 - 7.64 (m, 1 H) 7.70 (d, J=7.65 Hz, 1 H) 7.82 (d, J=8.41 Hz, 1 H) 7.97 (d, J=9.17 Hz, 1 H)
612		859.7	(500 MHz):0.47 - 0.61 (m, 3 H) 0.84 (d, J=7.13 Hz, 3 H) 0.86 (d, J=6.86 Hz, 3 H) 1.03 (d, J=7.40 Hz, 3 H) 1.12 (d, J=13.71 Hz, 1 H) 1.18 (s, 3 H) 1.18 - 1.23 (m, 1 H) 1.20 (d, J=6.03 Hz, 3 H) 1.24 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.42 (dd, J=15.08, 4.39 Hz, 1 H) 1.56 - 1.73 (m, 1 H) 1.80 - 1.90 (m, 1 H) 2.14 - 2.39 (m, 6 H) 2.31 (s, 6 H) 2.45 (s, 3 H) 2.47 - 2.59 (m, 2 H) 2.90 - 2.99 (m, 1 H) 3.07 (d, J=13.71 Hz, 1 H) 3.18 (s, 3 H) 3.19 - 3.23 (m, 1 H) 3.25 (s, 3 H) 3.40 - 3.48 (m, 2 H) 3.64 (d, J=7.95 Hz, 1 H) 3.80 (s, 2 H) 3.91 - 4.01 (m, 2 H) 4.16 - 4.24 (m, 1 H) 4.35 (d, J=7.13 Hz, 1 H) 4.39 - 4.50 (m, 1 H) 4.73 (d, J=4.94 Hz, 1 H) 5.01 - 5.11 (m, 1 H) 7.11 (s, 1 H) 7.13 - 7.18 (m, 1 H) 7.23 - 7.29 (m, 1 H) 7.37 (d, J=8.23 Hz, 1 H) 7.54 (d, J=7.95 Hz, 1 H)
613		823.7	(500 MHz):0.81 (d, J=7.13 Hz, 3 H) 0.83 (d, J=6.31 Hz, 3 H) 0.96 (d, J=7.40 Hz, 3 H) 1.08 (d, J=7.13 Hz, 3 H) 1.10 - 1.23 (m, 2 H) 1.18 - 1.22 (m, 6 H) 1.25 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.47 (dd, J=15.08, 4.94 Hz, 1 H) 1.58 - 1.67 (m, 1 H) 1.76 - 1.89 (m, 1 H) 2.19 - 2.32 (m, 4 H) 2.26 (s, 6 H) 2.31 - 2.38 (m, 1 H) 2.37 - 2.52 (m, 2 H) 2.40 (s, 3 H) 2.70 - 2.80 (m, 1 H) 2.91 - 3.01 (m, 1 H) 3.06 - 3.13 (m, 1 H) 3.14 - 3.19 (m, 1 H) 3.18 (s, 3 H) 3.29 (s, 3 H) 3.29 - 3.34 (m, 1 H) 3.39 - 3.50 (m, 1 H) 3.66 (d, J=8.23 Hz, 1 H) 3.70 - 3.79 (m, 1 H) 3.96 - 4.04 (m, 1 H) 4.05 - 4.10 (m, 1 H) 4.35 (d, J=7.13 Hz, 1 H) 4.51 - 4.72 (m, 1 H) 4.80 (d, J=4.39 Hz, 1 H) 4.94 - 5.06 (m, 1 H) 6.54 (d, J=9.60 Hz, 1 H) 7.36 (dd, J=9.60, 2.47 Hz, 1 H) 7.83 - 7.90 (m, 1 H)
614		820.6	(500 MHz):0.44 - 0.56 (m, 3 H) 0.84 (d, J=7.13 Hz, 3 H) 0.86 (d, J=6.86 Hz, 3 H) 1.03 (d, J=7.40 Hz, 3 H) 1.08 - 1.15 (m, 1 H) 1.17 (s, 3 H) 1.17 - 1.24 (m, 1 H) 1.20 (d, J=6.03 Hz, 3 H) 1.24 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.41 (dd, J=15.36, 4.66 Hz, 1 H) 1.59 - 1.72 (m, 1 H) 1.79 - 1.89 (m, 1 H) 2.17 - 2.28 (m, 4 H) 2.28 (s, 6 H) 2.33 - 2.39 (m, 1 H) 2.39 - 2.46 (m, 1 H) 2.45 (s, 3 H) 2.48 - 2.57 (m, 2 H) 2.94 (t, J=9.60 Hz, 1 H) 3.06 (d, J=14.81 Hz, 1 H) 3.18 (s, 3 H) 3.18 (s, 1 H) 3.25 (s, 3 H) 3.38 - 3.52 (m, 2 H) 3.64 (d, J=7.95 Hz, 1 H) 3.92 - 3.96 (m, 1 H) 3.96 - 4.02 (m, 1 H) 4.21 (dd, J=14.54, 3.29 Hz, 1 H) 4.35 (d, J=7.13 Hz, 1 H) 4.42 - 4.51 (m, 1 H) 4.73 (d, J=4.66 Hz, 1 H) 5.06 - 5.13 (m, 1 H) 6.44 - 6.48 (m, 1 H) 7.04 - 7.10 (m, 2 H) 7.16 - 7.22 (m, 1 H) 7.32 - 7.38 (m, 1 H) 7.54 - 7.61 (m, 1 H)

[1212] 

[Table 15-13]

615		795.6	(500 MHz):0.83 (d, J=7.26 Hz, 3 H) 0.86 (d, J=6.50 Hz, 3 H) 0.89 (d, J=6.88 Hz, 3 H) 1.08 (d, J=7.26 Hz, 3 H) 1.09 - 1.14 (m, 1 H) 1.19 - 1.25 (m, 1 H) 1.19 - 1.22 (m, 3 H) 1.21 (s, 3 H) 1.26 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.48 (dd, J=15.29, 4.97 Hz, 1 H) 1.61 - 1.67 (m, 1 H) 1.81 - 1.90 (m, 1 H) 2.22 - 2.35 (m, 5 H) 2.28 (s, 6 H) 2.41 (s, 3 H) 2.42 - 2.48 (m, 1 H) 2.48 - 2.55 (m, 1 H) 2.69 - 2.77 (m, 1 H) 2.98 (t, J=9.56 Hz, 1 H) 3.06 (d, J=13.76 Hz, 1 H) 3.16 - 3.20 (m, 1 H) 3.21 (s, 3 H) 3.29 (s, 3 H) 3.40 - 3.50 (m, 2 H) 3.67 (d, J=8.03 Hz, 1 H) 3.97 - 4.05 (m, 2 H) 4.17 - 4.23 (m, 1 H) 4.25 - 4.33 (m, 1 H) 4.37 (d, J=7.26 Hz, 1 H) 4.82 (d, J=4.59 Hz, 1 H) 4.97 - 5.08 (m, 1 H) 6.14 (dd, J=3.82, 2.68 Hz, 1 H) 6.76 (dd, J=3.82, 1.53 Hz, 1 H) 6.85 (dd, J=2.68, 1.53 Hz, 1 H)
616		849.6	(500 MHz): 0.85 (d, J=7.13 Hz, 3 H) 0.87 (d, J=6.58 Hz, 3 H) 1.00 (d, J=7.13 Hz, 3 H) 1.16 (s, 3 H) 1.17 - 1.20 (m, 1 H) 1.19 (d, J=6.03 Hz, 3 H) 1.21 - 1.24 (m, 1 H) 1.22 (d, J=6.31 Hz, 3 H) 1.24 (s, 3 H) 1.30 (s, 3 H) 1.41 (dd, J=15.50, 4.53 Hz, 1 H) 1.58 - 1.66 (m, 1 H) 1.82 - 1.95 (m, 1 H) 2.14 - 2.25 (m, 4 H) 2.26 (s, 6 H) 2.36 - 2.59 (m, 4 H) 2.47 (s, 3 H) 2.93 (t, J=8.91 Hz, 1 H) 3.04 (d, J=14.54 Hz, 1 H) 3.14 - 3.20 (m, 1 H) 3.17 (s, 3 H) 3.22 (s, 3 H) 3.36 - 3.52 (m, 2 H) 3.63 (d, J=7.95 Hz, 1 H) 3.87 - 4.06 (m, 2 H) 4.34 (d, J=7.13 Hz, 1 H) 4.36 - 4.46 (m, 1 H) 4.51 - 4.60 (m, 1 H) 4.68 - 4.76 (m, 1 H) 5.13 - 5.24 (m, 1 H) 6.71 (d, J=9.32 Hz, 1 H) 7.44 - 7.50 (m, 1 H) 7.71 (d, J=9.32 Hz, 1 H) 8.60 (d, J=6.31 Hz, 1 H) 8.73 (s, 1 H)
617		850.6	(500 MHz):0.81 (d, J=7.13 Hz, 3 H) 0.83 - 0.89 (m, 3 H) 1.06 (d, J=7.40 Hz, 3 H) 1.07 - 1.13 (m, 1 H) 1.16 (s, 3 H) 1.17 - 1.24 (m, 1 H) 1.19 (d, J=6.03 Hz, 3 H) 1.23 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.39 (dd, J=15.08, 4.39 Hz, 1 H) 1.59 - 1.66 (m, 1 H) 1.78 - 1.88 (m, 1 H) 2.18 - 2.30 (m, 4 H) 2.26 (s, 6 H) 2.34 - 2.52 (m, 3 H) 2.44 (s, 3 H) 2.72 - 2.81 (m, 1 H) 2.93 (t, J=9.46 Hz, 1 H) 3.09 - 3.20 (m, 2 H) 3.17 (s, 3 H) 3.24 (s, 3 H) 3.26 - 3.38 (m, 1 H) 3.39 - 3.49 (m, 1 H) 3.64 (d, J=8.23 Hz, 1 H) 3.88 - 4.05 (m, 3 H) 4.34 (d, J=7.13 Hz, 1 H) 4.49 - 4.62 (m, 1 H) 4.73 (d, J=4.39 Hz, 1 H) 4.96 - 5.11 (m, 1 H) 7.27 (m, 3 H) 7.44 (dd, J=7.95, 4.66 Hz, 1 H) 8.26 (s, 1 H) 8.60 (dd, J=7.95, 1.92 Hz, 1 H) 8.97 (dd, J=4.39, 1.92 Hz, 1 H)
618		798.4	(600 MHz): 0.78-0.84 (m, 6 H) 0.87 (d, J=6.42 Hz, 3 H) 1.07 (d, J=7.34 Hz, 3 H) 1.06 - 1.11 (m, 1 H) 1.16 - 1.25 (m, 1 H) 1.19 (s, 3 H) 1.21 (d, J=5.96 Hz, 3 H) 1.26 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.43 - 1.49 (m, 1 H) 1.61 - 1.67 (m, 1 H) 1.77 - 1.84 (m, 1 H) 2.22 - 2.49 (m, 7 H) 2.27 (s, 6 H) 2.41 (s, 3 H) 2.66 - 2.72 (m, 1 H) 2.97 (t, J=9.86 Hz, 1 H) 3.06 - 3.11 (m, 1 H) 3.14 - 3.20 (m, 1 H) 3.19 (s, 3 H) 3.27 (s, 3 H) 3.40 - 3.49 (m, 2 H) 3.63 - 3.72 (m, 2 H) 3.97 - 4.04 (m, 1 H) 4.07 - 4.11 (m, 1 H) 4.35 (d, J=7.34 Hz, 1 H) 4.60-4.69 (m, 1 H) 4.81 (d, J=4.58 Hz, 1 H) 5.02 - 5.08 (m, 1 H) 6.09 - 6.14 (m, 1 H) 6.51 (d, J=8.71 Hz, 1 H) 7.26 - 7.31 (m, 2 H)

[1213] 

[Table 15-14]

619		815.4	(600 MHz):0.78 - 0.85 (m, 6 H) 1.03 (d, J=7.34 Hz, 3 H) 1.06 - 1.24 (m, 8 H) 1.08 (d, J=7.34 Hz, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.50 (dd, J=15.13, 4.59 Hz, 1 H) 1.61 - 1.68 (m, 1 H) 1.79 - 1.87 (m, 1 H) 2.20 - 2.34 (m, 5 H) 2.28 (s, 6 H) 2.38 (s, 3 H) 2.42 - 2.50 (m, 2 H) 2.70 - 2.76 (m, 1 H) 2.99 (t, J=9.86 Hz, 1 H) 3.06 (d, J=15.59 Hz, 1 H) 3.15 - 3.22 (m, 1 H) 3.20 (s, 3 H) 3.29 (s, 3 H) 3.40 - 3.48 (m, 2 H) 3.62 - 3.70 (m, 2 H) 3.99 - 4.05 (m, 1 H) 4.07 - 4.13 (m, 1 H) 4.23 - 4.30 (m, 1 H) 4.36 (d, J=7.34 Hz, 1 H) 4.84 (d, J=4.59 Hz, 1 H) 4.96 - 5.04 (m, 1 H) 5.66 (d, J=8.25 Hz, 1 H) 7.22 (d, J=7.79 Hz, 1 H) 8.64 (br. s., 1 H)
620		798.4	(600 MHz):0.79 - 0.88 (m, 6 H) 0.94 (d, J=6.88 Hz, 3 H) 1.08 (d, J=7.34 Hz, 3 H) 1.08 (s, 8 H) 1.27 (d, J=6.42 Hz, 3 H) 1.32 (s, 3 H) 1.47 - 1.53 (m, 1 H) 1.58 - 1.68 (m, 1 H) 1.80 - 1.87 (m, 1 H) 2.17 - 2.53 (m, 7 H) 2.28 (s, 6 H) 2.39 (s, 3 H) 2.68 - 2.74 (m, 1 H) 2.98 (t, J=10.09 Hz, 1 H) 3.09 - 3.22 (m, 2 H) 3.20 (s, 3 H) 3.29 (s, 3 H) 3.31 - 3.48 (m, 2 H) 3.67 (d, J=8.25 Hz, 1 H) 3.88 - 4.06 (m, 4 H) 4.36 (d, J=7.34 Hz, 1 H) 4.82 (d, J=4.59 Hz, 1 H) 4.91 - 5.01 (m, 1 H) 6.35 (d, J=7.79 Hz, 2 H) 7.24 - 7.27 (m, 2 H)
621		763.4	(500 MHz):0.79 - 0.86 (m, 6 H) 1.10 (d, J=7.26 Hz, 3 H) 1.16 (d, J=7.26 Hz, 3 H) 1.17 - 1.24 (m, 2 H) 1.19 (d, J=6.12 Hz, 3 H) 1.22 (d, J=6.12 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.35 - 1.43 (m, 1 H) 1.45 - 1.50 (m, 1 H) 1.54 (dd, J=15.29, 4.97 Hz, 1 H) 1.57 - 1.71 (m, 2 H) 1.73 - 1.81 (m, 1 H) 1.82 - 1.90 (m, 1 H) 2.11 - 2.21 (m, 1 H) 2.23 - 2.39 (m, 4 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.43 - 2.53 (m, 2 H) 2.76 - 2.84 (m, 1 H) 2.92 (d, J=14.91 Hz, 1 H) 3.01 (t, J=9.94 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.43 (m, 1 H) 3.44 - 3.51 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.76 - 3.84 (m, 1 H) 4.01 - 4.09 (m, 1 H) 4.14 (br. s., 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.73 (br. s., 1 H) 4.93 (d, J=4.59 Hz, 1 H)
622		763.4	(500 MHz):0.79 - 0.86 (m, 6 H) 1.10 (d, J=7.64 Hz, 3 H) 1.16 (d, J=7.26 Hz, 3 H) 1.18 (d, J=6.12 Hz, 3 H) 1.20 - 1.26 (m, 2 H) 1.22 (d, J=6.12 Hz, 3 H) 1.22 - 1.24 (m, 3 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.37 - 1.45 (m, 1 H) 1.45 - 1.73 (m, 4 H) 1.78 - 1.95 (m, 2 H) 2.11 - 2.20 (m, 1 H) 2.22 - 2.36 (m, 4 H) 2.29 (s, 6 H) 2.38 (s, 3 H) 2.41 - 2.53 (m, 2 H) 2.75 - 2.84 (m, 1 H) 2.93 (d, J=13.76 Hz, 1 H) 3.01 (t, J=9.75 Hz, 1 H) 3.16 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.43 - 3.51 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.77 - 3.85 (m, 1 H) 4.00 - 4.09 (m, 1 H) 4.15 (br, s., 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.75 (br, s., 1 H) 4.93 (d, J=4.59 Hz, 1 H)

[1214] 

[Table 15-15]

623		790.4	(500 MHz):0.84 - 0.92 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.15 (d, J=7.40 Hz, 3 H) 1.19 - 1.29 (m, 2 H) 1.21 (d, J=6.03 Hz, 3 H) 1.22 - 1.25 (m, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.08, 4.94 Hz, 1 H) 1.58 - 1.70 (m, 1 H) 1.86 - 1.97 (m, 1 H) 2.20 - 2.31 (m, 3 H) 2.28 - 2.31 (m, 6 H) 2.32 - 2.38 (m, 2 H) 2.34 - 2.35 (m, 3 H) 2.40 - 2.49 (m, 1 H) 2.50 - 2.58 (m, 1 H) 2.76 - 2.85 (m, 1 H) 2.89 (d, J=14.26 Hz, 1 H) 2.97 - 3.04 (m, 1 H) 3.20 (dd, J=10.15, 7.13 Hz, 1 H) 3.25 (s, 3 H) 3.26 - 3.30 (m, 1 H) 3.31 (s, 3 H) 3.44 - 3.50 (m, 1 H) 3.50 - 3.60 (m, 3 H) 3.68 - 3.77 (m, 2 H) 3.98 - 4.08 (m, 2 H) 4.22 - 4.29 (m, 2 H) 4.41 (d, J=7.13 Hz, 1 H) 4.92 (d, J=4.39 Hz, 1 H) 5.09 (br. s., 1 H)
624		804.4	(600 MHz):0.77 - 0.85 (m, 6 H) 1.09 (d, J=7.34 Hz, 3 H) 1.17 (d, J=7.34 Hz, 3 H) 1.19 - 1.26 (m, 2 H) 1.21 (d, J=5.96 Hz, 3 H) 1.22 (s, 3 H) 1.28 (d, J=6.42 Hz, 3 H) 1.31 (s, 3 H) 1.52 (dd, J=15.36, 4.81 Hz, 1 H) 1.61 - 1.69 (m, 1 H) 1.72 - 1.88 (m, 2 H) 1.99 - 2.10 (m, 1 H) 2.10 - 2.21 (m, 1 H) 2.21 - 2.36 (m, 4 H) 2.28 (s, 6 H) 2.37 (s, 3 H) 2.41 - 2.50 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.96 - 3.04 (m, 2 H) 3.17 - 3.22 (m, 1 H) 3.21 (s, 3 H) 3.23 - 3.30 (m, 2 H) 3.31 (s, 3 H) 3.37 - 3.43 (m, 1 H) 3.43 - 3.49 (m, 1 H) 3.55 (t, J=8.25 Hz, 2 H) 3.69 (d, J=8.25 Hz, 1 H) 4.00 - 4.07 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.28 - 4.35 (m, 2 H) 4.37 (d, J=7.34 Hz, 1 H) 4.72 - 4.79 (m, 1 H) 4.90 (d, J=4.58 Hz, 1 H)
625		818.5	(500 MHz):0.77 - 0.87 (m, 6 H) 1.10 (d, J=7.26 Hz, 3 H) 1.16 (d, J=7.26 Hz, 3 H) 1.19 - 1.28 (m, 8 H) 1.28 (d, J=6.50 Hz, 3 H) 1.32 (s, 3 H) 1.45 - 1.70 (m, 5 H) 1.72 - 1.81 (m, 1 H) 1.81 - 1.88 (m, 1 H) 2.09 - 2.19 (m, 1 H) 2.21 - 2.38 (m, 4 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.39 - 2.52 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.88 - 2.96 (m, 1 H) 2.98 - 3.04 (m, 1 H) 3.17 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.24 - 3.29 (m, 2 H) 3.32 (s, 3 H) 3.35 - 3.42 (m, 1 H) 3.43 - 3.49 (m, 1 H) 3.51 - 3.56 (m, 2 H) 3.70 (d, J=8.03 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.32 (t, J=8.03 Hz, 2 H) 4.39 (d, J=7.26 Hz, 1 H) 4.74 (br. s., 1 H) 4.93 (d, J=4.59 Hz, 1 H).
626		853.4	(500 MHz):0.77 - 0.84 (m, 6 H) 1.08 (d, J=7.40 Hz, 3 H) 1.11 (d, J=7.68 Hz, 3 H) 1.20 - 1.25 (m, 2 H) 1.22 (d, J=6.31 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 1.53 (dd, J=15.22, 4.80 Hz, 1 H) 1.57 - 1.65 (m, 1 H) 1.77 - 1.92 (m, 2 H) 2.07 - 2.19 (m, 1 H) 2.20 - 2.53 (m, 18 H) 2.74 - 2.82 (m, 1 H) 2.93 - 3.03 (m, 2 H) 3.17 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.42 - 3.50 (m, 1 H) 3.68 (d, J=7.95 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.09 - 4.17 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.66 - 4.76 (m, 1 H) 4.91 (d, J=4.39 Hz, 1 H) 5.08 - 5.13 (m, 2 H) 7.28 - 7.39 (m, 5 H)

[1215] 

[Table 15-16]

627		762.5	(500 MHz):0.79 - 0.87 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.16 (d, J=7.40 Hz, 3 H) 1.20 - 1.25 (m, 2 H) 1.21 (d, J=6.03 Hz, 3 H) 1.23 (s, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.54 (dd, J=15.08, 4.94 Hz, 1 H) 1.62 - 1.69 (m, 1 H) 1.80 - 1.96 (m, 2 H) 2.00 - 2.11 (m, 1 H) 2.12 - 2.34 (m, 7 H) 2.28 (s, 6 H) 2.38 (s, 3 H) 2.42 - 2.51 (m, 2 H) 2.74 - 2.84 (m, 1 H) 2.91 - 2.97 (m, 1 H) 3.00 (t, J=9.87 Hz, 1 H) 3.15 - 3.22 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.35 - 3.41 (m, 1 H) 3.42 - 3.50 (m, 1 H) 3.70 (d, J=8.23 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.12 (br. s., 1 H) 4.39 (d, J=7.40 Hz, 1 H) 4.79 (br. s., 1 H) 4.91 (d, J=4.66 Hz, 1 H) 5.35 (br. s., 1 H) 5.66 (br. s., 1 H)
628		772.5	(500 MHz):0.77-0.86 (m, 6 H) 1.09 (d, J=7.64 Hz, 3 H) 1.17 (d, J=7.26 Hz, 3 H) 1.20 - 1.28 (m, 8 H) 1.28 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.38 - 1.73 (m, 6 H) 1.75 - 1.91 (m, 2 H) 2.09 - 2.20 (m, 1 H) 2.22 - 2.41 (m, 16 H) 2.41 - 2.53 (m, 2 H) 2.75 - 2.85 (m, 1 H) 2.89 - 2.96 (m, 1 H) 3.00 (t, J=9.94 Hz, 1 H) 3.15 - 3.21 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.43 - 3.50 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.99 - 4.09 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.74 (br. s., 1 H) 4.93 (d, J=4.59 Hz, 1 H)
629		761.5	(500 MHz):0.77 - 0.87 (m, 6 H) 1.09 (d, J=7.13 Hz, 3 H) 1.12 - 1.27 (m, 2 H) 1.17 (d, J=7.40 Hz, 3 H) 1.20 - 1.25 (m, 6 H) 1.28 (d, J=6.31 Hz, 3 H) 1.31 (s, 3 H) 1.46 - 1.63 (m, 2 H) 1.77 - 1.91 (m, 2 H) 1.92 - 2.05 (m, 1 H) 2.13 (s, 3 H) 2.14 - 2.19 (m, 1 H) 2.20 - 2.40 (m, 13 H) 2.42 - 2.55 (m, 4 H) 2.76 - 2.83 (m, 1 H) 2.89 - 2.96 (m, 1 H) 3.00 (t, J=9.87 Hz, 1 H) 3.16 - 3.26 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.43 - 3.51 (m, 1 H) 3.69 (d, J=7.95 Hz, 1 H) 3.99 - 4.08 (m, 1 H) 4.10 - 4.18 (m, 1 H) 4.39 (d, J=7.13 Hz, 1 H) 4.65 - 4.76 (m, 1 H) 4.90 - 4.95 (m, 1 H)
630		853.6	(500 MHz): 0.76-0.84 (m, 6 H) 1.09 (d, J=7.40 Hz, 3 H) 1.11 - 1.25 (m, 8 H) 1.14 (d, J=7.40 Hz, 3 H) 1.18 (dd, J=6.17, 3.43 Hz, 3 H) 1.28 (d, J=6.31 Hz, 3 H) 1.32 (s, 3 H) 1.33 - 1.45 (m, 1 H) 1.45 - 1.77 (m, 5 H) 1.79 - 1.91 (m, 1 H) 2.07 - 2.19 (m, 1 H) 2.20 - 2.38 (m, 13 H) 2.39 - 2.56 (m, 2 H) 2.75 - 2.83 (m, 1 H) 2.86 - 2.95 (m, 1 H) 2.97 - 3.03 (m, 1 H) 3.14 - 3.25 (m, 1 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.36 - 3.43 (m, 1 H) 3.44 - 3.55 (m, 2 H) 3.70 (d, J=7.95 Hz, 1 H) 3.98 - 4.09 (m, 1 H) 4.12 - 4.19 (m, 1 H) 4.38 (d, J=7.13 Hz, 1 H) 4.42 (d, J=11.79 Hz, 1 H) 4.56 (d, J=11.79 Hz, 1 H) 4.63 - 4.74 (m, 1 H) 4.93 (d, J=4.66 Hz, 1 H) 7.26 - 7.35 (m, 5 H)

[1216] 

[Table 15-17]

631		784.6	(500 MHz):0.73 - 0.84 (m, 6 H) 1.11 (d, J=7.26 Hz, 3 H) 1.19 - 1.31 (m, 2 H) 1.19 - 1.22 (m, 3 H) 1.22 (d, J=6.12 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.33 (s, 3 H) 1.53 - 1.57 (m, 1 H) 1.63 - 1.71 (m, 1 H) 1.79 - 1.87 (m, 1 H) 1.87 - 1.96 (m, 1 H) 2.04 - 2.12 (m, 1 H) 2.22 - 2.38 (m, 5 H) 2.30 (s, 6 H) 2.35 (s, 3 H) 2.38 - 2.45 (m, 1 H) 2.46 - 2.54 (m, 1 H) 2.82 - 2.89 (m, 1 H) 2.94 - 3.05 (m, 2 H) 3.17 - 3.24 (m, 1 H) 3.22 (s, 3 H) 3.33 (s, 3 H) 3.38 - 3.44 (m, 1 H) 3.44 - 3.51 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.78 - 3.87 (m, 1 H) 3.93 - 4.01 (m, 1 H) 4.02 - 4.10 (m, 1 H) 4.14 - 4.21 (m, 1 H) 4.39 (d, J=6.88 Hz, 1 H) 4.67 - 4.75 (m, 1 H) 4.94 (d, J=4.20 Hz, 1 H) 6.10 - 6.16 (m, 2 H) 6.58 - 6.63 (m, 2 H)
632		798.6	(500 MHz):0.77-0.84 (m, 6 H) 1.09 (d, J=7.26 Hz, 3 H) 1.10 - 1.13 (m, 1 H) 1.16 (d, J=7.26 Hz, 3 H) 1.22 (d, J=6.12 Hz, 3 H) 1.23 - 1.26 (m, 1 H) 1.23 (s, 3 H) 1.29 (d, J=6.12 Hz, 3 H) 1.32 (s, 3 H) 1.39 - 1.48 (m, 1 H) 1.49 - 1.88 (m, 6 H) 2.04 - 2.15 (m, 1 H) 2.19 - 2.38 (m, 13 H) 2.39 - 2.44 (m, 1 H) 2.45 - 2.55 (m, 1 H) 2.75 - 2.84 (m, 1 H) 2.87 - 2.95 (m, 1 H) 2.97 - 3.04 (m, 1 H) 3.19 - 3.28 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.43 - 3.52 (m, 1 H) 3.70 (d, J=8.03 Hz, 1 H) 3.81 - 3.95 (m, 2 H) 4.00 - 4.08 (m, 1 H) 4.11 - 4.17 (m, 1 H) 4.39 (d, J=7.26 Hz, 1 H) 4.69 - 4.78 (m, 1 H) 4.93 (d, J=4.20 Hz, 1 H) 6.00 - 6.21 (m, 2 H) 6.55 - 6.67 (m, 2 H)
633		882.5	(500 MHz):0.81 (d, J=6.88 Hz, 6 H) 1.09 (d, J=7.65 Hz, 3 H) 1.12 - 1.25 (m, 2 H) 1.14 (d, J=7.65 Hz, 3 H) 1.20 - 1.23 (m, 6 H) 1.28 (d, J=6.12 Hz, 3 H) 1.31 (s, 3 H) 1.41 - 1.59 (m, 4 H) 1.62 - 1.69 (m, 1 H) 1.71 - 1.81 (m, 1 H) 1.80 - 1.89 (m, 1 H) 2.07 - 2.18 (m, 1 H) 2.21 - 2.38 (m, 4 H) 2.29 (s, 6 H) 2.34 (s, 3 H) 2.39 - 2.52 (m, 2 H) 2.73 - 2.82 (m, 1 H) 2.86 - 2.95 (m, 1 H) 3.00 (t, J=9.94 Hz, 1 H) 3.13 - 3.26 (m, 3 H) 3.22 (s, 3 H) 3.32 (s, 3 H) 3.34 - 3.42 (m, 1 H) 3.43 - 3.50 (m, 1 H) 3.69 (d, J=7.65 Hz, 1 H) 3.98 - 4.09 (m, 1 H) 4.09 - 4.17 (m, 1 H) 4.38 (d, J=7.65 Hz, 1 H) 4.71 (br. s., 1 H) 4.77 - 4.84 (m, 1 H) 4.92 (d, J=4.59 Hz, 1 H) 5.08 (s, 2 H) 7.27 - 7.39 (m, 5 H)
634		898 FAB MASS	(300 MHz) : 0.80 - 0.92 (m, 6 H) 1.10 (d, J=7.42 Hz, 3 H) 1.16 (d, J=7.42 Hz, 3 H) 1.18 - 1.26 (m, 2 H) 1.23 (d, J=6.32 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.54 (dd, J=5.00 Hz, 15.4Hz, 1 H) 1.53 - 1.58 (m, 1 H) 1.64 - 1.73 (m, 1 H) 1.85 - 1.94 (m, 1 H) 2.17 - 2.40 (m, 12 H) 2.41 - 2.54 (m, 2 H) 2.75 - 2.87 (m, 1 H) 2.91 - 3.06 (m, 2 H) 3.21 (dd, J=7.42 Hz, 10.2 Hz, 1 H) 3.24 (s, 3 H) 3.32 (s, 3 H) 3.26 - 3.56 (m, 4 H) 3.65 (t, J=4.40 Hz, 2 H) 3.70 (d, J=7.69 Hz, 1 H) 3.99 - 4.14 (m, 2 H) 4.20 - 4.29 (m, 1 H) 4.40 (d, J=7.14 Hz, 1 H) 4.56 (s, 2 H) 4.76 - 4.88 (m, 1 H) 4.90 (d, J=4.40 Hz, 1 H) 7.25 - 7.39 (m, 5 H)

[1217] 

[Table 15-18]

635		802.2	(300 MHz) : 0.80 - 0.92 (m, 6 H) 1.10 (d, J=7.14 Hz, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.23 (d, J=6.04 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.55 (dd, J=4.95 Hz, 15.1 Hz, 1 H) 1.62 - 1.72 (m, 1 H) 1.81 - 1.94 (m, 1 H) 2.17 - 2.40 (m, 12 H) 2.41 - 2.54 (m, 3 H) 2.75 - 2.87 (m, 1 H) 2.94 - 3.07 (m, 2 H) 3.21 (dd, J=6.87 Hz, 10.2 Hz, 1 H) 3.24 (s, 3 H) 3.26 - 3.58 (m, 7 H) 3.71 (d, J=7.97 Hz, 1 H) 3.99 - 4.14 (m, 2 H) 4.41 (d, J=7.14 Hz, 1 H) 4.56 (s, 2 H) 4.60 - 4.74 (m, 2 H) 4.77 - 4.94 (m, 2 H) 5.10 - 5.22 (m, 1 H)
636		808 FAB MASS	(300 MHz) : 0.81 - 0.94 (m, 6 H) 1.11 (d, J=7.14 Hz, 3 H) 1.18 (d, J=7.42 Hz, 3 H) 1.23 (d, J=7.69 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.55 (dd, J=4.67 Hz, 15.1 Hz, 1 H) 1.62 - 1.71 (m, 1 H) 1.81 - 1.94 (m, 1 H) 2.17 - 2.58 (m, 14 H) 2.75 - 2.87 (m, 1 H) 2.94 - 3.07 (m, 2 H) 3.21 (dd, J=6.87 Hz, 10.2 Hz, 1 H) 3.24 (s, 3 H) 3.30 - 3.39 (m, 4 H) 3.40 - 3.62 (m, 2 H) 3.71 (d, J=7.69 Hz, 1 H) 3.75 - 3.85 (m, 3 H) 3.99 - 4.19 (m, 2 H) 4.21 - 4.30 (m, 2 H) 4.41 (d, J=7.14 Hz, 1 H) 4.56 (s, 2 H) 4.80 - 4.94 (m, 2 H) 5.28 - 5.38 (m, 1 H)
637		758 FAB MASS	(300 MHz) : 0.90 - 1.05 (m, 6 H) 1.14 (d, J=7.42 Hz, 3 H) 1.18 - 1.39 (m, 15 H) 1.55 (dd, J=4.67 Hz, 15.1 Hz 1 H) 1.60 - 1.74 (m, 1 H) 1.75 - 1.87 (m, 1 H) 2.05 - 2.42 (m, 12 H) 2.45 - 2.56 (m, 1 H) 2.61 - 2.83 (m, 2 H) 2.98 - 3.08 (m, 1 H) 3.24 - 3.44 (m, 8 H) 3.47 - 3.60 (m, 1 H) 3.81 (d, J=6.87 Hz, 1 H) 3.97 - 4.09 (m, 1 H) 4.24 - 4.34 (m, 1 H) 4.53 (d, J=7.14 Hz, 1 H) 4.62 (d, J=4.40 Hz, 1 H) 4.87 - 5.20 (m, 1 H)
638		791.2	(300 MHz): 0.82 (d, J=6.86 Hz, 6 H) 1.06 - 1.92 (m, 17 H) 1.10 (d, J=7.41 Hz, 3H) 1.16 (d, J=7.41 Hz, 3H) 1.23 (d, J=6.04 Hz, 3H) 1.24 (s, 3 H) 1.29 (d, J=6.32 Hz, 3 H) 2.08 - 2.52 (m, 6 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.73 - 2.87 (m, 1 H) 2.91 (d, J=14.55 Hz, 1 H) 3.01 (t, J=9.89 Hz, 1 H) 3.15 - 3.25 (m, 2 H) 3.23 (s , 3 H) 3.33 (s, 3 H) 3.37 - 3.54 (m, 2 H) 3.64 (t, J=6.59 Hz, 2 H) 3.70 (d, J=8.25 Hz, 1 H) 4.00 - 4.19 (m, 2 H) 4.39 (d, J=7.14 Hz, 1 H) 4.66 - 4.76 (m, 1 H) 4.94 (d, J=4.40 Hz, 1 H)

[1218] 

[Table 15-19]

639		777.3	(300 MHz): 0.83 (d, J=6.86 Hz, 6 H) 1.08 - 1.92 (m, 15 H) 1.10 (d, J=7.41 Hz, 3H) 1.16 (d, J=7.42 Hz, 3 H) 1.23 (d, J=6.04 Hz, 3H) 1.24 (s, 3 H) 1.29 (d, J=6.59 Hz, 3 H) 1.33 (s, 3 H) 2.07 - 2.53 (m, 6 H) 2.29 (s, 6 H) 2.37 (s, 3 H) 2.72 - 2.86 (m, 1 H) 2.91 (d, J=14.56 Hz, 1 H) 2.98 (t, J=9.88 Hz, 1 H) 3.16 - 3.27 (m, 2 H) 3.23 (s , 3 H) 3.33 (s, 3 H) 3.37 - 3.53 (m, 2 H) 3.63 (t, J=6.60 Hz, 2 H) 3.71 (d, J=8.24 Hz, 1 H) 4.00 - 4.20 (m, 2 H) 4.40 (d, J=7.42 Hz, 1 H) 4.65 - 4.80 (m, 1 H) 4.94 (d, J=4.40 Hz, 1 H)
640		858	(300 MHz) : 0.84 (d, J=6.86 Hz, 6 H) 0.87 (d, J=4.67 Hz, 3 H) 1.03 - 1.36 (m, 2 H) 1.03 (d, J=7.42 Hz, 3H) 1.08 (d, J=7.14 Hz, 3H) 1.21 (s, 3 H) 1.22 (d, J=6.05 Hz, 3H) 1.28 (d, J=6.32 Hz, 3H) 1.33 (s, 3 H) 1.50 (dd, J=4.67, 14.84 Hz, 1 H) 1.59 - 1.75 (m, 1 H) 1.81 - 1.94 (m, 1 H) 2.22 - 2.36 (m, 5 H) 2.28 (s, 6 H) 2.43 (s, 3 H) 2.43 - 2.56 (m, 2 H) 2.65 - 2.86 (m, 2 H) 2.93 - 3.06 (m, 2 H) 3.16 - 3.24 (m, 2 H) 3.25 (s , 3 H) 3.28 (s, 3 H) 3.36 - 3.54 (m, 2 H) 3.70 (d, J=7.97 Hz, 1 H) 3.97 - 4.16 (m, 2 H) 4.38 (d, J=7.14 Hz, 1 H) 4.90 (d, J=4.67 Hz, 1 H) 4.95 - 5.03 (m, 1 H) 6.30 - 6.43 (m, 1 H) 6.59 (d, J=15.93 Hz, 1 H), 7.49 - 7.56 (m, 1 H), 7.63 - 7.69 (m, 1 H), 7.78 (d, J=8.24 Hz, 1 H), 7.98 (d, J=1.93 Hz, 1 H), 8.06 (d, J=8.52 Hz, 1 H), 8.94 (d, J=2.20 Hz, 1 H)
641		803	mixture of diastereomers, (300 MHz) : 0.85 (d, J=6.87 Hz, 6 H) 1.07 - 1.79 (m, 9 H) 1.09 (d, J=7.42 Hz, 3 H) 1.16 (d, J=7.42 Hz, 3 H) 1.23 (d, J=6.04 Hz, 3 H) 1.24 (s, 3 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.80 - 2.57 (m, 6 H) 2.33 (s, 6 H) 2.42 (s, 3 H) 2.71 - 2.82 (m, 1 H) 2.96 - 3.09 (m, 2 H) 3.17 - 3.39 (m, 2 H) 3.25 (s , 3 H) 3.32 (s , 3 H) 3.42 - 3.54 (m, 1 H) 3.71 (d, J=7.97 Hz, 1 H) 3.98 - 4.19 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.92 (d, J=4.39 Hz, 1 H) 5.01 - 5.11 (m, 1 H)
642		825	(300 MHz): 0.79 - 2.70 (m, 18 H) 0.79 (d, J=7.15 Hz, 3 H) 0.89 (d, J=6.87 Hz, 3 H) 1.04 (d, J=7.42 Hz, 3 H) 1.22 (d, J=4.40 Hz, 3 H) 1.24 (s, 3 H) 1.26 (d, J=6.32 Hz, 3 H) 1.30 (s, 3 H) 1.49 (s, 3 H) 2.35 (s, 9 H) 2.91 - 3.09 (m, 2 H) 3.20 - 3.33 (m, 2 H) 3.25 (s , 3 H) 3.29 (s , 3 H) 3.33 - 3.54 (m, 2 H) 3.70 (d, J=7.15 Hz, 1 H) 3.90 - 4.07 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.76 (d, J=3.85 Hz, 1 H) 4.95 - 5.07 (m, 1 H) 7.18 - 7.34 (m, 3 H) 7.46 (d, J=7.14 Hz, 2 H)

[1219] 

[Table 15-20]

643		777	mixture of diastereomers, (300 MHz) : 0.80 - 0.94 (m, 9 H) 1.10 - 1.74 (m, 9 H) 1.10 (d, J=7.15 Hz, 3 H) 1.16 (s, 3 H) 1.17 (d, J=6.04 Hz, 3 H) 1.23 (d, J=5.77 Hz, 3 H) 1.24 (s, 3 H) 1.30 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.79 - 2.55 (m, 6 H) 2.31 (s, 6 H) 2.43 (s, 3 H) 2.71 - 2.84 (m, 1 H) 2.95 - 3.10 (m, 2 H) 3.18 - 3.42 (m, 2 H) 3.25 (s , 3 H) 3.32 (s , 3 H) 3.42 - 3.53 (m, 1 H) 3.71 (d, J=7.97Hz, 1 H) 4.00 - 4.21 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.93 (d, J=4.39 Hz, 1 H) 4.99 - 5.08 (m, 1 H)
644		749 FAB MASS	mixture of diastereomers, (300 MHz) : 0.82 - 0.95 (m, 6 H) 1.07 - 1.49 (m, 22 H) 1.49 - 1.98 (m, 5 H) 2.14 - 2.62 (m, 16 H) 2.74 - 2.87 (m, 1 H)2.87 - 3.11 (m, 3 H) 3.16 - 3.31 (m, 4 H) 3.33 and 3.34 (s, 3 H) 3.38 - 3.55 (m, 2 H) 3.59 - 3.69 and 3.81 - 3.93 (m, 1 H) 3.73 (d, J=7.69 Hz, 1 H) 3.99 - 4.17 (m, 2 H) 4.37 - 4.46 (m, 1 H)
645		779	(300 MHz) : 0.78 - 0.92 (m, 6 H) 1.10 (d, J=7.14 Hz, 3 H) 1.16 (d, J=7.42 Hz, 3 H) 1.10 (d, J=7.14 Hz, 3 H) 1.19 - 1.27 (m, 6 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.37 - 1.98 (m, 6 H) 2.11 - 2.35 (m, 9 H) 2.38 (s, 3 H) 2.41 - 2.53 (m, 2 H) 2.74 - 2.86 (m, 1 H) 2.89 - 3.00 (m, 1 H) 3.02 (t, J= 10.2 Hz 1H) 3.17 - 3.30 (m, 5 H) 3.33 (s, 3 H) 3.36 - 3.54 (m, 2 H) 3.59 - 3.77 (m, 3 H) 4.00 - 4.18 (m, 2 H) 4.39 (d, J=7.42 Hz, 1 H) 4.70 - 4.83 (m, 1 H) 4.93 (d, J=4.4 Hz, 1 H)
646		804	(300 MHz) : 0.92 (d, J=6.32 Hz, 3 H) 1.07 (d, J=7.14 Hz, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.21 - 1.29 (m, 7 H) 1.32 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.55 (dd, J=4.95 Hz, 15.7 Hz 1 H) 1.59 - 1.67 (m, 1 H) 1.86 - 1.99 (m, 1 H) 2.11 - 2.20 (m, 1 H) 2.16 (s, 3 H) 2.23 - 2.41 (m, 9 H) 2.43 - 2.60 (m, 3 H) 2.91 - 3.10 (m, 3 H) 3.21 - 3.49 (m, 9 H) 3.50 - 3.66 (m, 2 H) 3.81 (d, J=6.04 Hz, 1 H) 4.03 - 4.15 (m, 1 H) 4.49 - 4.57 (m, 3 H) 4.60 (d, J=7.14 Hz, 1 H) 5.15 - 5.31 (m, 2 H) 5.31 - 5.43 (m, 1 H) 5.81 - 5.96 (m, 1 H) 7.00 (br s, 1 H)
647		858.4	(400 MHz) : 0.94 - 1.04 (m, 6 H) 1.05 - 1.36 (m, 2 H) 1.13 (d, J=9.01 Hz, 3 H) 1.15 (s, 3 H) 1.19 (d, J=6.82 Hz, 3H) 1.24 (d, J=6.09 Hz, 3H) 1.28 (d, J=6.33 Hz, 3H) 1.31 (s, 3 H) 1.61 - 1.90 (m, 3 H) 2.05 - 3.04 (m, 11 H) 2.25 (s, 3 H) 2.31 (s, 6 H) 3.24 - 3.43 (m, 3 H) 3.30 (s , 3 H) 3.38 (s, 3 H) 3.47 - 3.60 (m, 2 H) 3.83 (d, J=6.82 Hz, 1 H) 3.97 - 4.08 (m, 1 H) 4.27 - 4.35 (m, 1 H) 4.47 - 4.57 (m, 1 H) 4.60 (d, J=4.62 Hz, 1 H) 5.02 - 5.29 (m, 1 H) 6.33 - 6.44 (m, 1 H) 6.62 (d, J=16.07 Hz, 1 H) 7.53(t, J=7.06 Hz, 1 H) 7.67 (dd, J=7.06, 8.52 Hz, 1 H) 7.78 (d, J=8.28 Hz, 1 H) 7.99 (s, 1 H) 8.06 (d, J=8.53 Hz, 1 H) 8.96 (d, J=1.46 Hz, 1 H)

[1220] 

[Table 15-21]

648		858.5	(300 MHz) : 0.94 - 1.06 (m, 6 H) 1.08 - 1.32 (m, 2 H) 1.10 (s, 3 H) 1.30 (s, 3 H) 1.44 - 1.79 (m, 3 H) 2.03 - 3.04 (m, 11 H) 2.27 (s, 3 H) 2.33 (s, 6 H) 3.15 - 3.58 (m, 3 H) 3.27 (s , 3 H) 3.37 (s, 3 H) 3.82 (d, J=6.60 Hz, 1 H) 3.91 - 4.01 (m, 1 H) 4.27 - 4.35 (m, 1 H) 4.47 - 4.55 (m, 2 H) 6.37 - 6.49 (m, 1 H) 7.20 (d, J=15.38 Hz, 1 H) 7.42(d, J=4.67 Hz, 1 H) 7.53 - 7.60 (m, 1 H) 7.68 - 7.77 (m, 1 H) 8.10 (d, J=9.34 Hz, 2 H) 8.84 (d, J=4.67 Hz, 1 H)
649		797.4	(300 MHz) : 0.96 (d, J=6.87 Hz, 3 H) 1.03 (d, J=5.76 Hz, 3 H) 1.05 - 1.37 (m, 2 H) 1.13 (d, J=7.42 Hz, 6 H) 1.22 (s, 3 H) 1.23 (d, J=4.39 Hz, 3 H) 1.26 (d, J=6.31 Hz, 3 H) 1.33 (s, 3 H) 1.50 (dd, J=4.95, 15.11 Hz, 1 H) 1.55 - 1.76 (m, 2 H) 1.95 - 2.06 (m, 1 H) 2.16 - 2.51 (m, 5 H) 2.28 (s, 6 H) 2.40 (s, 3 H) 2.75 - 2.92 (m, 3 H) 2.93 - 3.05 (m, 2 H) 3.17 - 3.38 (m, 3 H) 3.28 (s , 3 H) 3.32 (s, 3 H) 3.40 - 3.56 (m, 2 H) 3.77 (d, J=6.59 Hz, 1 H) 3.96 - 4.18 (m, 2 H) 4.40 (d, J=7.42 Hz, 1 H) 4.75 (d, J=4.40 Hz, 1 H) 4.84 - 4.93 (m, 1 H) 6.76 - 6.88 (m, 2 H) 7.06 - 7.16 (m, 2 H)
650		818	(300 MHz) : 0.79 - 0.90 (m, 6 H) 1.11 (d, J=7.14 Hz, 3 H) 1.18 (d, J=7.42 Hz, 3 H) 1.21 - 1.27 (m, 6 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.55 (dd, J=4.95 Hz, 15.4 Hz, 1 H) 1.60 - 1.81 (m, 2 H) 1.81 - 1.96 (m, 1 H) 2.12 - 2.33 (m, 8 H) 2.33 - 2.41 (m, 4 H) 2.41 - 2.53 (m, 2 H) 2.75 - 2.87 (m, 1 H) 2.88 - 3.07 (m, 3 H) 3.17 - 3.29 (m, 5 H) 3.30 - 3.54 (m, 5 H) 3.71 (d, J=7.69 Hz, 1 H) 4.00 - 4.18 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.55 (d, J=5.77 Hz, 2 H) 4.79 - 4.90 (m, 1 H) 4.92 (d, J=4.40 Hz, 1 H) 5.07 (br s, 1 H) 5.18 - 5.35 (m, 2 H) 5.84 - 5.99 (m, 1 H)
651		869 FAB MASS	(300 MHz) : 0.73 - 0.89 (m, 9 H) 1.06 (d, J=7.14 Hz, 3 H) 1.17 - 1.25 (m, 6 H) 1.27 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.47 (dd, J=4.67 Hz, 15.1 Hz, 1 H) 1.56 - 1.71 (m, 2 H) 1.77 - 1.92 (m, 1 H) 2.18 - 2.33 (m, 14 H) 2.39 - 2.54 (m, 4 H) 2.57 - 2.69 (m, 1 H) 2.77 (dd, J=3.57 Hz, 13.7 Hz, 1 H) 2.94 - 3.10 (m, 3 H) 3.15 - 3.25 (m, 5 H) 3.28 (s, 3 H) 3.39 - 3.53 (m, 2 H) 3.67 (d, J=7.97 Hz, 1 H) 3.81 (s, 3 H) 3.96 - 4.09 (m, 2 H) 4.36 (d, J=7.14 Hz. 1 H) 4.84 (d, J=4.40 Hz, 2 H) 4.90 - 5.02 (m, 1 H) 6.74 - 6.83 (m, 2 H) 6.92 (d, J=7.97 Hz, 1 H)

[1221] 

[Table 15-22]

652		802.5	(300 MHz) : 0.92 (d, J=6.60 Hz, 3 H) 1.07 (d, J=7.42 Hz, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.21 - 1.30 (m, 12 H) 1.33-1.41 (m, 4 H) 1.33 (s, 3 H) 1.56 - 1.75 (m, 2 H) 1.86 - 1.98 (m, 1 H) 2.11 - 2.19 (m, 3 H) 2.20 - 2.39 (m, 10 H) 2.42 (t, J=2.47 Hz, 3 H) 2.44 - 2.58 (m, 3 H) 2.94 - 3.07 (m, 2 H) 3.12 (t, J=9.89 Hz, 1 H) 3.24 - 3.48 (m, 9 H) 3.50 - 3.64 (m, 2 H) 3.81 (d, J=6.32 Hz, 1 H) 4.04 - 4.16 (m, 1 H) 4.52 (d, J=4.95 Hz, 1 H) 4.54 - 4.66 (m, 3 H) 5.30 - 5.42 (m, 1 H)
653		827 FAB MASS	(300 MHz) : 0.76 - 0.89 (m, 9 H) 1.07 (d, J=7.42 Hz, 3 H) 1.17 - 1.25 (m, 6 H) 1.27 (d, J=6.32 Hz, 3 H) 1.32 (s, 3 H) 1.48 (dd, J=4.95 Hz, 15.4 Hz, 1 H) 1.60 - 1.92 (m, 3 H) 2.19 - 2.35 (m, 9 H) 2.38 - 2.54 (m, 5 H) 2.60 - 2.75 (m, 2 H) 2.91 - 3.04 (m, 3 H) 3.16 - 3.25 (m, 5 H) 3.29 (s, 3 H) 3.39 - 3.53 (m, 2 H) 3.68 (d, J=7.97 Hz, 1 H) 3.87 (s, 3 H) 3.97 - 4.10 (m, 2 H) 4.37 (d, J=7.14 Hz, 1 H) 4.85 (d, J=4.40 Hz, 2 H) 4.88 - 4.98 (m, 1 H) 6.65 - 6.72 (m, 2 H) 6.80 (d, J=7.97 Hz, 1 H)
654		811.4	mixture of diastereomers, (400 MHz) : 0.82 - 0.91 (m, 6 H) 1.07 - 1.38 (m, 14 H) 1.25 (s, 3 H) 1.34 (s, 3 H) 1.57 (dd, J=4.88, 15.35 Hz, 1 H) 1.66 (d, J=12.66 Hz, 1 H) 1.73 - 2.02 (m, 3 H) 2.15 - 2.63 (m, 15 H) 2.29 (s, 6 H) 2.77 - 2.93 (m, 1 H) 2.94 - 3.12 (m, 2 H) 3.18 - 3.38 (m, 5 H) 3.34 (s, 3 H) 3.38 - 3.61 (m, 2 H) 3.73 (d, J=7.80 Hz, 1 H) 4.01 - 4.22 (m, 2 H) 4.37 - 4.45 (m, 1 H) 4.55 - 4.78 (m, 1 H) 4.75 - 5.22 (m, 1 H) 4.88 - 4.97 (m, 1 H) 7.24 - 7.37 (m, 5 H)
655		791.5	mixture of diastereomers, (400 MHz) : 0.82 - 0.94 (m, 9 H) 1.08 - 1.98 (m, 27 H) 1.24 (s, 3 H) 1.55 (dd, J=4.87, 15.34 Hz, 1 H) 2.19 - 2.56 (m, 9 H) 2.29 (s, 6 H) 2.75 - 2.86 (m, 1 H) 2.87 - 3.08 (m, 3 H) 3.18 - 3.28 (m, 2 H) 3.26 (s 3 H) 3.32 - 3.35 (m, 2 H) 3.37 - 3.58 (m, 2 H) 3.62 - 3.73 (m, 1 H) 3.73 (d, J=8.03 Hz, 1 H) 4.00 - 4.17 (m, 2 H) 4.34 - 4.45 (m, 1 H) 4.88 - 5.11 (m, 2 H)
656		777.5	mixture of diastereomers, (400 MHz): 0.79 - 0.94 (m, 12 H) 1.09 - 1.35 (m, 14 H) 1.24 (s, 3 H) 1.32 (s, 3 H) 1.41 - 1.49 (m, 1 H) 1.55 (dd, J=4.87, 15.10 Hz, 1 H) 1.60 - 1.96 (m, 4 H) 2.19 - 2.54 (m, 9 H) 2.29 (s, 6 H) 2.74 - 2.86 (m, 1 H) 2.89 - 3.07 (m, 2 H) 3.14 - 3.27 (m, 2 H) 3.25 (s , 3 H) 3.34 (s , 3 H) 3.38 - 3.55 (m, 2 H) 3.73 (d, J=7.80 Hz, 1 H) 4.00 - 4.19 (m, 2 H) 4.41 (d, J=7.06 Hz, 1 H) 4.87 - 5.10 (m, 2 H)

[1222] 

[Table 15-23]

657		777.5	mixture of diastereomers, (400 MHz) : 0.81 - 0.95 (m, 9 H) 1.08 - 1.97 (m, 25 H) 1.24 (s, 3 H) 1.55 (dd, J=4.39, 15.11 Hz, 1 H) 2.16 - 2.54 (m, 9 H) 2.29 (s, 6 H) 2.74 - 2.87 (m, 1 H) 2.89 - 3.08 (m, 2 H) 3.17 - 3.30 (m, 2 H) 3.26 (s , 3 H) 3.32 - 3.35 (m, 3 H) 3.38 - 3.56 (m, 2 H) 3.60 - 3.75 (m, 1 H) 3.72 (d, J=7.80 Hz, 1 H) 4.01 - 4.18 (m, 2 H) 4.37 - 4.46 (m, 1 H) 4.88 - 5.12. (m, 2 H)
658		832.6	(300 MHz) : 0.78 - 0.88 (m, 6 H) 1.10 (d, J=7.14 Hz, 3 H) 1.16 (d, J=7.42 Hz, 3 H) 1.19 - 1.27 (m, 6 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.43 - 1.91 (m, 4 H) 2.09 - 2.41 (m, 12 H) 2.41 - 2.53 (m, 2 H) 2.74 - 2.85 (m, 1 H) 2.87 - 2.97 (m, 1 H) 3.02 (t, J=9.34 Hz, 1 H) 3.13 - 3.26 (m, 5 H) 3.33 (s, 3 H) 3.36 - 3.53 (m, 2 H) 3.70 (d, J=7.97 Hz, 1 H) 4.00 - 4.18 (m, 2 H) 4.39 (d, J=7.14 Hz, 1 H) 4.55 (d, J=5.77 Hz, 2 H) 4.68 - 4.83 (m, 2 H) 4.93 (d, J=4.40 Hz, 1 H) 5.17 - 5.35 (m, 2 H) 5.84 - 6.00 (m, 1 H)
659		806.6	(300 MHz) : 0.78 - 0.88 (m, 6 H) 1.10 (d, J=7.14 Hz, 3 H) 1.16 (d, J=7.42 Hz, 3 H) 1.19 - 1.27 (m, 6 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.42 - 1.91 (m, 4 H) 2.09 - 2.41 (m, 12 H) 2.41 - 2.54 (m, 2 H) 2.74 - 2.85 (m, 1 H) 2.87 - 2.97 (m, 1 H) 3.02 (t, J=9.34 Hz, 1 H) 3.13 - 3.27 (m, 5 H) 3.33 (s, 3 H) 3.36 - 3.53 (m, 2 H) 3.66 (s, 3 H) 3.70 (d, J=7.97 Hz, 1 H) 4.00 - 4.19 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.68 - 4.79 (m, 2 H) 4.93 (d, J=4.40 Hz, 1 H)
660		830.3	(300 MHz) : 0.77 - 0.90 (m, 6 H) 1.10 (d, J=7.42 Hz, 3 H) 1.16 (d, J=7.14 Hz, 3 H) 1.20 - 1.27 (m, 6 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.43 - 1.94 (m, 4 H) 2.10 - 2.41 (m, 12 H) 2.41 - 2.56 (m, 3 H) 2.74 - 2.85 (m, 1 H) 2.89 - 3.06 (m, 2 H) 3.15 - 3.28 (m, 5 H) 3.33 (s, 3 H) 3.36 - 3.54 (m, 2 H) 3.70 (d, J=7.97 Hz, 1 H) 4.00 - 4.18 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.63 - 4.78 (m, 3 H) 4.88 (br s, 1 H) 4.93 (d, J=4.12 Hz, 1 H)
661		827.4	(300 MHz) : 0.91 - 1.06 (m, 6 H) 1.06 - 1.17 (m, 6 H) 1.19 - 1.31 (m, 9 H) 1.34 (s, 3 H) 1.51 (dd, J=4.67 Hz, 15.4 Hz, 1 H) 1.64 - 1.73 (m, 1 H) 1.94 - 2.09 (m, 1 H) 2.13 - 2.35 (m, 9 H) 2.35 - 2.54 (m, 6 H) 2.75 - 2.90 (m, 2 H) 2.93 - 3.04 (m, 2 H) 3.18 - 3.36 (m, 8 H) 3.43 - 3.56 (m, 2 H) 3.67 - 3.81 (m, 4 H) 3.96 - 4.07 (m, 1 H) 4.09 - 4.18 (m, 1 H) 4.41 (d, J=7.14 Hz, 1 H) 4.76 (d, J=4.40 Hz, 2 H) 4.87 - 4.97 (m, 1 H) 6.61 - 6.75 (m, 2 H) 6.81 (d, J=8.52 Hz, 1 H)

[1223] 

[Table 15-24]

662		841.5	(300 MHz) : 0.79 - 0.92 (m, 6 H) 1.12 (d, J=7.14 Hz, 3 H) 1.15 - 1.27 (m, 11 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.56 (dd, J=4.95 Hz, 15.1 Hz, 1 H) 1.62 - 1.71 (m, 1 H) 1.80 - 1.98 (m, 2 H) 2.12 - 2.38 (m, 9 H) 2.38 - 2.60 (m, 5 H) 2.77 - 2.88 (m, 1 H) 2.97 - 3.09 (m, 2 H) 3.17 - 3.27 (m, 4 H) 3.27 - 3.37 (m, 4 H) 3.39 - 3.54 (m, 2 H) 3.72 (d, J=7.97 Hz, 1 H) 3.80 (s, 3 H) 4.00 - 4.18 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.66 - 4.82 (m, 2 H) 4.91 (d, J=4.67 Hz, 1 H) 6.87 (d, J=8.79 Hz, 1 H) 7.23 (d, J=8.79 Hz, 1 H)
663		776 FAB MASS	(300 MHz) : 0.77 - 0.88 (m, 6 H) 1.10 (d, J=7.42 Hz, 3 H) 1.17 (d, J=7.42 Hz, 3 H) 1.19 - 1.27 (m, 8 H) 1.29 (d, J=6.32 Hz, 3 H) 1.33 (s, 3 H) 1.49 - 1.92 (m, 4 H) 2.11 - 2.33 (m, 10 H) 2.33 - 2.41 (m, 4 H) 2.41 - 2.54 (m, 2 H) 2.75 - 2.86 (m, 1 H) 2.87 - 2.97 (m, 1 H) 3.02 (t, J=9.07 Hz, 1 H) 3.17 - 3.26 (m, 5 H) 3.33 (s, 3 H) 3.35 - 3.54 (m, 2 H) 3.71 (d, J=7.97 Hz, 1 H) 4.00 - 4.17 (m, 2 H) 4.40 (d, J=7.14 Hz, 1 H) 4.71 - 4.84 (m, 1 H) 4.93 (d, J=4.40 Hz, 1 H) 5.31 (br s, 1 H) 5.55 (br s, 1 H)

Example 567

[1224] 

(1) By using the compound obtained in Example 1 (9.0 g) and the compound obtained in Reference Example 160 (8.52 g) as starting materials, a cyclized compound (2.57 g) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) The compound obtained in (1) mentioned above (2.25 g) was dissolved in methanol (110 ml), the solution was added with 5% palladium-carbon (51 mg), and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was added with saturated aqueous sodium hydrogencarbonate and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain an amine compound (1.92 g).

(3) The compound obtained in (2) mentioned above (100 mg) was dissolved in a mixed solvent of chloroform-methanol (2:1, 3 ml), the solution was added with benzoic acid (34 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg) and 4-dimethylaminopyridine (11.2 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 90:10:0.2 to 30:10:0.2) to obtain an amide compound (96.9 mg).

(4) By using the compound obtained in (3) mentioned above (93.9 mg) as a starting material, the compound shown in Table 15 (66.4 mg) was obtained in the same manner as that of Example 7, (4).

Example 568

[1225] By using the compound obtained in Example 567, (2) (100 mg) and nicotinic acid (34 mg) as starting materials, the compound shown in Table 15 (41.5 mg) was obtained in the same manners as those of Example 567, (3) and Example 7, (4).

Example 569

[1226] By using the compound obtained in Example 567, (2) (100 mg) and quinoline-5-carboxylic acid (47.6 mg) as starting materials, the compound shown in Table 15 (25.7 mg) was obtained in the same manners as those of Example 567, (3) and Example 7, (4).

Example 570

[1227] By using the compound obtained in Example 567, (2) (100 mg) and isoquinoline-5-carboxylic acid (47.6 mg) as starting materials, the compound shown in Table 15 (31.1 mg) was obtained in the same manners as those of Example 567, (3) and Example 7, (4).

Example 571

[1228] 

(1) The compound obtained in Example 567, (2) (100 mg) was dissolved in chloroform (2 ml), the solution was added with 3-furancarboxylic acid (30.8 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg) and 4-dimethylaminopyridine (11.2 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 90:10:0.2 to 30:10:0.2) to obtain an amide compound (91.2 mg).

(2) By using the compound obtained in (1) mentioned above (89.5 mg) as a starting material, the compound shown in Table 15 (38.4 mg) was obtained in the same manner as that of Example 7, (4).

Example 572

[1229] By using the compound obtained in Example 567, (2) (100 mg) and 3-thenoic acid (35.2 mg) as starting materials, the compound shown in Table 15 (39.5 mg) was obtained in the same manner as that of Example 571, (1) and Example 7, (4).

Example 573

[1230] By using the compound obtained in Example 567, (2) (100 mg) and pyrazinecarboxylic acid (34.1 mg) as starting materials, the compound shown in Table 15 (52.4 mg) was obtained in the same manners as those of Example 571, (1) and Example 7, (4).

Example 574

[1231] By using the compound obtained in Example 567, (2) (100 mg) and cinnoline-4-carboxylic acid (47.9 mg) as starting materials, the compound shown in Table 15 (24.9 mg) was obtained in the same manners as those of Example 571, (1) and Example 7, (4).

Example 575

[1232] By using the compound obtained in Example 567, (2) (100 mg) and 4-pyridazinecarboxylic acid (34.1 mg) as starting materials, the compound shown in Table 15 (42.9 mg) was obtained in the same manners as those of Example 571, (1) and Example 7, (4).

Example 576

[1233] By using the compound obtained in Example 567, (2) (101 mg) and indole-3-carboxylic acid (44.9 mg) as starting materials, the compound shown in Table 15 (33.1 mg) was obtained in the same manners as those of Example 571, (1) and Example 7, (4).

Example 577

[1234] By using the compound obtained in Example 567, (2) (100 mg) and indazole-3-carboxylic acid (44.6 mg) as starting materials, the compound shown in Table 15 (39.2 mg) was obtained in the same manners as those of Example 571, (1) and Example 7, (4).

Example 578

[1235] 

(1) The compound obtained in Example 567, (2) (88 mg) was dissolved in chloroform (2 ml), the solution was added with 1-isoquinolinecarboxylic acid (41.9 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (46.2 mg), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 100:10:0.2 to 30:10:0.2) to obtain an amide compound (55.9 mg).

(2) By using the compound obtained in (1) mentioned above (53.9 mg) as a starting material, the compound shown in Table 15 (35.5 mg) was obtained in the same manner as that of Example 7, (4).

Example 579

[1236] By using the compound obtained in Example 567, (2) (88 mg) and quinoline-8-carboxylic acid (41.9 mg) as starting materials, the compound shown in Table 15 (43.9 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 580

[1237] By using the compound obtained in Example 567, (2) (88 mg) and [1,8]naphthylidine-4-carboxylic acid (42.2 mg) as starting materials, the compound shown in Table 15 (29.0 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 581

[1238] By using the compound obtained in Example 567, (2) (88 mg) and [1,6]naphthylidine-5-carboxylic acid (42.2 mg) as starting materials, the compound shown in Table 15 (27.2 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 582

[1239] By using the compound obtained in Example 567, (2) (88 mg) and picolinic acid (29.8 mg) as starting materials, the compound shown in Table 15 (30.1 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 583

[1240] By using the compound obtained in Example 567, (2) (63 mg) and isonicotinic acid (21.4 mg) as starting materials, the compound shown in Table 15 (19.4 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 584

[1241] By using the compound obtained in Example 567, (2) (100 mg) and 5-pyrimidinecarboxylic acid (34.1 mg) as starting materials, the compound shown in Table 15 (28.2 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 585

[1242] By using the compound obtained in Example 567, (2) (100 mg) and 1H-indene-3-carboxylic acid (44.1 mg) as starting materials, the compound shown in Table 15 (43 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 586

[1243] By using the compound obtained in Example 567, (2) (100 mg) and 1-benzofuran-3-carboxylic acid (44.6 mg) as starting materials, the compound shown in Table 15 (72 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 587

[1244] By using the compound obtained in Example 567, (2) (100 mg) and 1-benzothiophene-3-carboxylic acid (49 mg) as starting materials, the compound shown in Table 15 (38 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 588

[1245] By using the compound obtained in Example 567, (2) (100 mg) and indole-4-carboxylic acid (44.3 mg) as starting materials, the compound shown in Table 15 (57.1 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 589

[1246] By using the compound obtained in Example 567, (2) (100 mg) and indole-7-carboxylic acid (44.3 mg) as starting materials, the compound shown in Table 15 (44.1 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 590

[1247] By using the compound obtained in Example 567, (2) (100 mg) and 2-furancarboxylic acid (30.8 mg) as starting materials, the compound shown in Table 15 (51.1 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 591

[1248] By using the compound obtained in Example 567, (2) (100 mg) and pyrrole-2-carboxylic acid (30.6 mg) as starting materials, the compound shown in Table 15 (52.9 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 592

[1249] By using the compound obtained in Example 567, (2) (100 mg) and 2-thenoic acid (35.2 mg) as starting materials, the compound shown in Table 15 (35.8 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 593

[1250] By using the compound obtained in Example 567, (2) (100 mg) and 4-pyrazolecarboxylic acid (30.8 mg) as starting materials, the compound shown in Table 15 (42.6 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 594

[1251] By using the compound obtained in Example 567, (2) (100 mg) and 1,2,3-thiadiazole-4-carboxylic acid (35.8 mg) as starting materials, the compound shown in Table 15 (68.6 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 595

[1252] By using the compound obtained in Example 567, (2) (100 mg) and 1H-[1,2,4]triazole-3-carboxylic acid (31.1 mg) as starting materials, the compound shown in Table 15 (12.2 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 596

[1253] By using the compound obtained in Example 567, (2) (100 mg) and 4-imidazolecarboxylic acid (30.8 mg) as starting materials, the compound shown in Table 15 (13.6 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 597

[1254] By using the compound obtained in Example 567, (2) (100 mg) and isoxazole-5-carboxylic acid (31.1 mg) as starting materials, the compound shown in Table 15 (17.2 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 598

[1255] By using the compound obtained in Example 567, (2) (100 mg) and 1,2,5-oxadiazole-3-carboxylic acid (31.4 mg) as starting materials, the compound shown in Table 15 (9.3 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 599

[1256] By using the compound obtained in Example 567, (2) (100 mg) and 4-thiazolecarboxylic acid (35.5 mg) as starting materials, the compound shown in Table 15 (14.2 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 600

[1257] By using the compound obtained in Example 567, (2) (100 mg) and pyrrole-3-carboxylic acid monohydrate (30.6 mg) as starting materials, the compound shown in Table 15 (31.1 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 601

[1258] By using the compound obtained in Example 567, (2) (100 mg) and thiazole-2-carboxylic acid (35.5 mg) as starting materials, the compound shown in Table 15 (51.6 mg) was obtained in the same manners as those of Example 578, (1) and Example 7, (4).

Example 602

[1259] By using the compound obtained in Example 1 (480 mg) and the compound obtained in Reference Example 161 (470 mg) as starting materials, the compound shown in Table 15 (49 mg) was obtained in the same manner as that of Example 7.

Example 603

[1260] By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 162 (1.62 g) as starting materials, the compound shown in Table 15 (148 mg) was obtained in the same manner as that of Example 7.

Example 604

[1261] 

(1) The compound obtained in Example 52, (1) (140 mg) was dissolved in dimethylformamide (5 ml), the solution was added with 2,4-oxazolidinedione (65.3 mg) and potassium carbonate (179 mg), and the mixture was stirred at 120°C for 1.5 hours. The reaction mixture was added with ethyl acetate and distilled water, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 60:10:0.2) to obtain an N-alkyl compound (101 mg).

(2) By using the compound obtained in (1) mentioned above (98.0 mg) as a starting material, the compound shown in Table 15 (45.8 mg) was obtained in the same manner as that of Example 7, (4).

Example 605

[1262] By using the compound obtained in Example 52, (1) (130 mg) and 2-hydroxypyrimidine (157 mg) as starting materials, the compound shown in Table 15 (42.5 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 606

[1263] By using the compound obtained in Example 52, (1) (130 mg) and 2-hydroxypyrimidine (157 mg) as starting materials, the compound shown in Table 15 (12.3 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 607

[1264] By using the compound obtained in Example 52, (1) (150 mg) and 4-hydroxyquinazoline (101 mg) as starting materials, the compound shown in Table 15 (77.3 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 608

[1265] By using the compound obtained in Example 52, (1) (750 mg) and 2-hydroxypyridine (330 mg) as starting materials, the compound shown in Table 15 (108 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 609

[1266] By using the compound obtained in Example 52, (1) (150 mg) and 2-quinolinol (101 mg) as starting materials, the compound shown in Table 15 (43.2 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 610

[1267] By using the compound obtained in Example 52, (1) (150 mg) and 3-cyanoindole (98.5 mg) as starting materials, the compound shown in Table 15 (71.0 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 611

[1268] By using the compound obtained in Example 52, (1) (150 mg) and 2-quinolinol (101 mg) as starting materials, the compound shown in Table 15 (32.6 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 612

[1269] By using the compound obtained in Example 52, (1) (150 mg) and 3-indoleacetonitrile (108 mg) as starting materials, the compound shown in Table 15 (16.1 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 613

[1270] By using the compound obtained in Example 52, (1) (150 mg) and 6-oxo-1,6-dihydro-3-pyridinecarbonitrile (83.5 mg) as starting materials, the compound shown in Table 15 (74.3 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 614

[1271] By using the compound obtained in Example 52, (1) (300 mg) and indole (162 mg) as starting materials, the compound shown in Table 15 (37.8 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 615

[1272] By using the compound obtained in Example 52, (1) (150 mg) and pyrrole-2-carbonitrile (63.8 mg) as starting materials, the compound shown in Table 15 (55.0 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 616

[1273] By using the compound obtained in Example 52, (1) (150 mg) and 1,6-naphthylidin-2(1H)-one (101 mg) as starting materials, the compound shown in Table 15 (48.6 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 617

[1274] By using the compound obtained in Example 52, (1) (150 mg) and pyrido[2,3-d]pyrimidin-4(3H)-one (102 mg) as starting materials, the compound shown in Table 15 (76.6 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 618

[1275] By using the compound obtained in Example 52, (1) (150 mg) and 2-hydroxypyridine (132 mg) as starting materials, the compound shown in Table 15 (55 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 619

[1276] By using the compound obtained in Example 52, (1) (150 mg) and uracil (156 mg) as starting materials, the compound shown in Table 15 (44 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 620

[1277] By using the compound obtained in Example 52, (1) (150 mg) and 4-hydroxypyridine (132 mg) as starting materials, the compound shown in Table 15 (32 mg) was obtained in the same manners as those of Example 604, (1) and Example 7, (4).

Example 621

[1278] 

(1) By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 152 (1.55 g) as starting materials, a cyclized compound (276 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (170 mg) as a starting material, the compound shown in Table 15 (85.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 622

[1279] 

(1) By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 153 (1.45 g) as starting materials, a cyclized compound (244 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (176 mg) as a starting material, the compound shown in Table 15 (77.7 mg) was obtained in the same manner as that of Example 7, (4).

Example 623

[1280] By using the compound obtained in Example 1 (1.18 g) and the compound obtained in Reference Example 154 (511 mg) as starting materials, the compound shown in Table 15 (133 mg) was obtained in the same manner as that of Example 7.

Example 624

[1281] By using the compound obtained in Example 1 (811 mg) and the compound obtained in Reference Example 155 (385 mg) as starting materials, the compound shown in Table 15 (16.3 mg) was obtained in the same manner as that of Example 7.

Example 625

[1282] 

(1) By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 156 (1.22 g) as starting materials, a cyclized compound (314 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (250 mg) as a starting material, the compound shown in Table 15 (194 mg) was obtained in the same manner as that of Example 7, (4).

Example 626

[1283] 

(1) By using the compound obtained in Example 1 (3.0 g) and the compound obtained in Reference Example 157 (3.8 g) as starting materials, a cyclized compound (257 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) By using the compound obtained in (1) mentioned above (50.1 mg) as a starting material, the compound shown in Table 15 (25.1 mg) was obtained in the same manner as that of Example 7, (4).

Example 627

[1284] 

(1) The compound obtained in Example 626, (1) (102 mg) was dissolved in a mixed solvent of methanol-ethyl acetate (2:1, 3 ml), the solution was added with 5% palladium-carbon (51 mg), and the mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain a debenzylated compound (93.9 mg).

(2) The compound obtained in (1) mentioned above (30.6 mg) was dissolved in chloroform (1 ml), the solution was added with triethylamine (19.2 µl) and isobutyl chloroformate (18 µl) under ice cooling, and the mixture was stirred at the same temperature for 1 hour. The mixture was added with a 0.5 N solution of ammonia in 1,4-dioxane (0.83 ml), and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was neutralized with saturated aqueous ammonium chloride, and then the reaction mixture was added with chloroform and saturated aqueous ammonium chloride. The layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 60:10:0.2) to obtain an amide compound (40.7 mg).

(3) By using the compound obtained in (2) mentioned above (40.7 mg) as a starting material, the compound shown in Table 15 (10.0 mg) was obtained in the same manner as that of Example 7, (4).

Example 628

[1285] By using the compound obtained in Example 1 (1.50 g) and the compound obtained in Reference Example 158 (2.0 g) as starting materials, the compound shown in Table 15 (93 mg) was obtained in the same manner as that of Example 7.

Example 629

[1286] 

(1) By using the compound obtained in Example 1 (3.0 g) and the compound obtained in Reference Example 159 (3.0 g) as starting materials, a cyclized compound (514 mg) was obtained in the same manners as those of Example 7, (1), (2) and (3).

(2) The compound obtained in (1) mentioned above (200 mg) was dissolved in methanol (5 ml), the solution was added with 5% palladium-carbon (100 mg), and the mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (5 ml), the solution was added with 20% palladium hydroxide-carbon (500 mg), and the mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (4 ml), the solution was added with 20% palladium hydroxide-carbon (500 mg), and the mixture was stirred at room temperature for 1.5 hours under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine = 60=10:0.2) to obtain a debenzylated compound (73.9 mg).

(3) By using the compound obtained in (2) mentioned above (72.2 mg) as a starting material, a ketone compound (73.3 mg) was obtained in the same manner as that of Example 113, (2).

(4) By using the compound obtained in (3) mentioned above (73.3 mg) as a starting material, the compound shown in Table 15 (27.4 mg) was obtained in the same manner as that of Example 7, (4).

Example 630

[1287] By using the compound obtained in Example 629, (1) (130 mg) as a starting material, the compound shown in Table 15 (59.4 mg) was obtained in the same manner as that of Example 7, (4).

Example 631

[1288] By using the compound obtained in Example 1 (719 mg) and 1-(2-oxiran-2-ylethyl)-1H-pyrrole (497 mg) obtained by the method described in the literature (Journal of Organic Chemistry, 1987, vol. 52, 5, p.819) as starting materials, the compound shown in Table 15 ( 64.9 mg) was obtained in the same manner as that of Example 7.

Example 632

[1289] By using the compound obtained in Example 1 (604 mg) and 1-(3-oxiran-2-ylpropyl)-1H-pyrrole (460 mg) obtained by the method described in the literature (Journal of Organic Chemistry, 1987, vol. 52, 5, p.819) as starting materials, the compound shown in Table 15 (29.3 mg) was obtained in the same manner as that of Example 7.

Example 633

[1290] By using the compound obtained in Example 567, (1) (100 mg) as a starting material, the compound shown in Table 15 (67.6 mg) was obtained in the same manner as that of Example 7, (4).

Example 634

[1291] 

(1) The compound obtained in Example 1 (800 mg) was dissolved in tetrahydrofuran (5.4 ml), the solution was added with the compound obtained in Reference Example 199 (3.03 g) and ytterbium triflate monohydrate (50 mg), and the mixture was stirred at 90°C for 10 minutes under microwave irradiation. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 30:1 to chloroform:methanol:28% aqueous ammonia = 30:1:0.1) to obtain a 10a-N-(4-((2-(benzyloxy)ethoxy)carbonylamino)-2-hydroxypropyl) compound (290 mg).

(2) By using the compound obtained in (1) mentioned above (289 mg) as a starting material, a 10a-N-methyl compound (288 mg) was obtained in the same manner as that of Example 7, (2).

(3) Dimethylaminopyridine (83 mg) and 2-methyl-6-nitrobenzoic acid anhydride (117 mg) were dissolved in dichloromethane (24 ml), the solution was added dropwise with a solution of the compound obtained in (2) mentioned above (281 mg) in dichloromethane (16 ml) at room temperature over 1 hour and 20 minutes, and then the mixture was further stirred at room temperature for 1 hour. The reaction mixture was added with 20% aqueous ammonium chloride, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 5:1 to 2:1) to obtain a cyclized compound (148 mg).

(4) By using the compound obtained in (3) mentioned above (146 mg) as a starting material, the compound shown in Table 15 (104 mg) was obtained in the same manner as that of Example 7, (4).

Example 635

[1292] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 200 (1.87 g) as starting materials, the compound shown in Table 15 (76 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 636

[1293] By using the compound obtained in Example 634 (91 mg) as a starting material, the compound shown in Table 15 (15 mg) was obtained in the same manner as that of Example 81.

Example 637

[1294] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 42 (1.34 g) as starting materials, the compound shown in Table 15 (12.9 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 638

[1295] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 201 (3.12 g) as starting materials, the compound shown in Table 15 (105 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 639

[1296] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 202 (2.95 g) as starting materials, the compound shown in Table 15 (125 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 640

[1297] 

(1) By using the compound obtained in Example 1 (800 mg) and (R)-2-allyloxirane (1.02 g) obtained by the method described in the literature (Journal of American Chemical Society, 2004, vol. 126, p.2495) as starting materials, a cyclized compound (442 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2) and Example 634, (3).

(2) The compound obtained in (1) mentioned above (160 mg) was dissolved in a 2% solution of 1-methyl-2-pyrrolidinone in dioxane, the solution was added with trisdibenzylideneacetone dipalladium (13.7 mg), 3-bromoquinoline (40.5 mg), dicyclohexylmethylamine (63.5 µl) and a 0.52 N solution of tri-t-butylphosphine in dioxane (57.5 µl), and the mixture was stirred at 90°C for 1 hour under microwave irradiation. The reaction mixture was added with saturated aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:tetrahydrofuran = 20:1) to obtain a coupling compound (95.6 mg).

(3) By using the compound obtained in (2) mentioned above (95.6 mg) as a starting material, the compound shown in Table 15 (61.4 mg) was obtained in the same manner as that of Example 7, (4).

Example 641

[1298] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 203 (3.26 g) as starting materials, a mixture of deprotected compounds was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4). This mixture was dissolved in dimethylformamide (150 µl), the solution was added with 18-crown-6-ether (43.8 mg) and potassium fluoride (9.6 mg), and the mixture was stirred at 60°C for 26 hours. The reaction mixture was concentrated, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 5:1:0.1) to obtain the compound shown in Table 15 (10 mg).

Example 642

[1299] By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 204 (1.63 g) as starting materials, the compound shown in Table 15 (2.1 mg) was obtained in the same manner as that of Example 641.

Example 643

[1300] By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 205 (1.15 g) as starting materials, the compound shown in Table 15 (27.6 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 644

[1301] By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 206 (3.3 g) as starting materials, the compound shown in Table 15 (105 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 645

[1302] By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 207 (5.4 g) as starting materials, the compound shown in Table 15 (208 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 646

[1303] 

(1) By using the compound obtained in Example 1 (800 mg) and the compound obtained in Reference Example 208 (978 mg) as starting materials, a 10a-N-methyl compound (110 mg) was obtained in the same manners as those of Example 634, (1) and Example 7, (2).

(2) 2-Chloro-1-methylpyridinium iodide (37 mg) was dissolved in acetonitrile (23 ml), the solution was added dropwise with a solution of the compound obtained in (1) mentioned above (110 mg) and triethylamine (40 µl) in acetonitrile (10 ml) over 20 minutes under reflux by heating, and then the mixture was further stirred for 0.5 hour under reflux by heating. The reaction mixture was added with 20% aqueous ammonium chloride and ethyl acetate, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 15:1 to 10:1) to obtain a cyclized compound (36 mg).

(3) By using the compound obtained in (2) mentioned above (35 mg) as a starting material, the compound shown in Table 15 (22 mg) was obtained in the same manner as that of Example 7, (4).

Example 647

[1304] 

(1) By using the compound obtained in Example 1 (0.55 g) and the compound obtained in Reference Example 209 (441 mg) as starting materials, a cyclized compound (88.1 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2) and Example 646, (2).

(2) By using the compound obtained in (1) mentioned above (29.4 mg) and 3-bromoquinoline (7.4 µl) as starting materials, the compound shown in Table 15 (9.0 mg) was obtained in the same manners as those of Example 640, (2) and Example 7, (4).

Example 648

[1305] By using the compound obtained in Example 647, (1) (29.4 mg) and 4-bromoquinoline (28.5 mg) as starting materials, the compound shown in Table 15 (2.7 mg) was obtained in the same manners as those of Example 640, (2) and Example 7, (4).

Example 649

[1306] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 210 (3.99 g) as starting materials, the compound shown in Table 15 (198.9 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 650

[1307] By using the compound obtained in Example 1 (1.2 g) and the compound obtained in Reference Example 211 (1.64 g) as starting materials, the compound shown in Table 15 (134 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 651

[1308] 

(1) By using the compound obtained in Example 1 (1.2 g) and the compound obtained in Reference Example 212 (1.64 g) as starting materials, a cyclized compound (496 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2) and Example 634, (3).

(2) By using the compound obtained in (1) mentioned above (250 mg) as a starting material, the compound shown in Table 15 (170 mg) was obtained in the same manner as that of Example 7, (4).

Example 652

[1309] By using the compound obtained in Example 1 (2.0 g) and the compound obtained in Reference Example 200 (3.06 g) as starting materials, the compound shown in Table 15 (80 mg) was obtained in the same manners as those of Example 634, (1) Example 7, (2), Example 646, (2) and Example 7, (4).

Example 653

[1310] The compound obtained in Example 651 (30 mg) was dissolved in methanol (2 ml), and the solution was stirred for 19 hours under reflux by heating. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1) to obtain the compound shown in Table 15 (26 mg).

Example 654

[1311] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 213 (4.2 g) as starting materials, the compound shown in Table 15 (71.1 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 655

[1312] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 214 (3.9 g) as starting materials, the compound shown in Table 15 (76.0 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 656

[1313] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 215 (3.69 g) as starting materials, the compound shown in Table 15 (51.3 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 657

[1314] By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 216 (3.69 g) as starting materials, the compound shown in Table 15 (63 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 658

[1315] 

(1) The compound obtained in Example 54, (1) (50 mg) was dissolved in dichloromethane (1 ml), the solution was added with triethylamine (7.7 µl) and allyl chloroformate (5.4 µl), and the mixture was stirred for 1 hour under ice cooling. The reaction mixture was added with distilled water and chloroform, the layers were separated, and the organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 3:1) to obtain a carbamate compound (44 mg).

(2) By using the compound obtained in (1) mentioned above (43 mg) as a starting material, the compound shown in Table 15 (29 mg) was obtained in the same manner as that of Example 7, (4).

Example 659

[1316] By using the compound obtained in Example 54, (1) (40 mg) and methyl chloroformate (3.1 µl) as starting materials, the compound shown in Table 15 (24 mg) was obtained in the same manners as those of Example 658, (1) and Example 7, (4).

Example 660

[1317] By using the compound obtained in Example 54, (1) (40 mg) and propargyl alcohol (30 µl) as starting materials, the compound shown in Table 15 (5 mg) was obtained in the same manners as those of Example 54, (2) and Example 7, (4).

Example 661

[1318] By using the compound obtained in Example 1 (405 mg) and the compound obtained in Reference Example 217 (600 mg) as starting materials, the compound shown in Table 15 (23 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2), Example 634, (3) and Example 7, (4).

Example 662

[1319] 

(1) By using the compound obtained in Example 1 (1.0 g) and the compound obtained in Reference Example 218 (2.4 g) as starting materials, a cyclized compound (92 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2) and Example 634, (3).

(2) By using the compound obtained in (1) mentioned above (42 mg) as a starting material, the compound shown in Table 15 (13 mg) was obtained in the same manner as that of Example 7, (4).

Example 663

[1320] 

(1) By using the compound obtained in Example 1 (1.5 g) and the compound obtained in Reference Example 219 (3.3 g) as starting materials, a cyclized compound (349 mg) was obtained in the same manners as those of Example 634, (1), Example 7, (2) and Example 634, (3).

(2) By using the compound obtained in (1) mentioned above (150 mg) as a starting material, a carboxylic acid compound (138 mg) was obtained in the same manner as that of Example 64.

(3) By using the compound obtained in (2) mentioned above (75 mg) as a starting material, the compound shown in Table 15 (20 mg) was obtained in the same manners as those of Example 91, (2) and Example 7, (4).

Syntheses of Examples 664 to 668

[1321] Preparation methods of compounds represented by the formula (AC) having R^{1 A C} and R^{2 A C} defined in Table 16 are shown below.

[Table 16-1]

[1322] 

Table 16

Example	R1AC	R2AC	ESI MS (M+H)	1H-NMR, CDCl3, δ (ppm)
664			965.0	mixture of diastereomers(600 MHz): 0.76 - 0.88 (m, 6 H) 1.02 - 1.25 (m, 17 H) 1.26 - 1.34 (m, 8 H) 1.57 - 1.97 (m, 7 H) 2.10 - 2.32 (m, 3 H) 2.32 - 2.52 (m, 4 H) 2.35 (s, 3 H) 2.36 - 2.38 (m, 6 H) 2.53 - 2.61 (m, 1 H) 2.67 - 2.85 (m, 3 H) 2.93 - 3.01 (m, 1 H) 3.22 (s, 3 H) 3.29 - 3.45 (m, 3 H) 3.34 (s, 3 H) 3.58 - 3.74 (m, 3 H) 4.05 - 4.17 (m, 1 H) 4.31 - 4.40 (m, 1 H) 4.43 - 4.56 (m, 2 H) 4.69 - 4.79 (m, 1 H) 4.91 - 4.97 (m, 1 H) 5.37 - 5.45 (m, 1 H) 6.67 - 6.75 (m, 2 H) 6.88 - 6.93 (m, 1 H) 7.10 - 7.17 (m, 1 H), and (600 MHz): 0.76 - 0.88 (m, 6 H) 1.02 - 1.25 (m, 17 H) 1.26 - 1.34 (m, 8 H) 1.57 - 1.97 (m, 7 H) 2.10 - 2.32 (m, 3 H) 2.32 - 2.52 (m, 5 H) 2.36 - 2.38 (m, 6 H) 2.39 (s, 3 H) 2.67 - 2.85 (m, 3 H) 2.93 - 3.01 (m, 1 H) 3.01 - 3.09 (m, 1 H) 3.21 (s, 3 H) 3.35 (d, J=10.09 Hz, 3 H) 3.36 (s, 3 H) 3.58 - 3.74 (m, 3 H) 4.05 - 4.17 (m, 1 H) 4.31 - 4.40 (m, 1 H) 4.43 - 4.56 (m, 2 H) 4.69 - 4.79 (m, 1 H) 4.91 - 4.97 (m, 1 H) 5.09 - 5.15 (m, 1 H) 6.67 - 6.75 (m, 2 H) 6.88 - 6.93 (m, 1 H) 7.10 - 7.17 (m, 1 H)
665			964.9	(600 MHz): 0.76 - 0.84 (m, 6 H) 1.00 - 1.26 (m, 2 H) 1.07 (d, J=7.34 Hz, 3 H) 1.11 (d, J=6.42 Hz, 3 H) 1.13 - 1.16 (m, 6 H) 1.21 (s, 3 H) 1.27 (d, J=6.42 Hz, 3 H) 1.29 (s, 3 H) 1.53 - 1.98 (m, 7 H) 2.09 - 2.31 (m, 3 H) 2.32 - 2.51 (m, 5 H) 2.35 (s, 3 H) 2.37 (s, 6 H) 2.71 - 2.83 (m, 3 H) 2.95 (d, J=14.21 Hz, 1 H) 3.00 - 3.07 (m, 1 H) 3.20 (s, 3 H) 3.26 - 3.41 (m, 3 H) 3.34 (s, 3 H) 3.55 - 3.62 (m, 1 H) 3.63 - 3.70 (m, 2 H) 4.06 - 4.15 (m, 1 H) 4.29 - 4.39 (m, 1 H) 4.45 (d, J=7.34 Hz, 1 H) 4.51 (d, J=10.09 Hz, 1 H) 4.67 - 4.77 (m, 1 H) 4.93 (d, J=4.59 Hz, 1 H) 5.10 - 5.14 (m, 1 H) 6.65 - 6.71 (m, 2 H) 6.88 (s, 1 H) 7.10 (t, J=7.79 Hz, 1 H)

[1323] 

[Table 16-2]

666			1007.0	(600 MHz):0.77 - 0.85 (m, 6 H) 0.92 (t, J=6.88 Hz, 3 H) 1.06 - 1.25 (m, 2 H) 1.11 (d, J=7.34 Hz, 3 H) 1.13 (s, 3H) 1.14 - 1.19 (m, 9 H) 1.28 (d, J=6.88 Hz, 3 H) 1.30 (s, 3 H) 1.50 - 1.56 (m, 1 H) 1.56 - 1.97 (m, 6 H) 2.10 - 2.19 (m, 1 H) 2.20 - 2.31 (m, 2 H) 2.24 (s, 6 H) 2.31 - 2.65 (m, 9 H) 2.36 (s, 3 H) 2.76 - 2.84 (m, 1 H) 2.93 (d, J=15.59 Hz, 1 H) 3.12 - 3.42 (m, 4 H) 3.22 (s, 3 H) 3.31 (s, 3 H) 3.50 - 3.59 (m, 1 H) 3.70 (d, J=8.25 Hz, 1 H) 3.84 (s, 3 H) 4.17 (s, 1 H) 4.32 - 4.46 (m, 3 H) 4.53 (d, J=10.09 Hz, 1 H) 4.75 (s, 1 H) 4.94 (d, J=4.58 Hz, 1 H) 5.54 - 5.62 (m, 1 H) 6.86 (d, J=7.79 Hz, 1 H) 6.90 (t, J=7.57 Hz, 1 H) 7.19 (t, J=6.88 Hz, 1 H) 7.27 (d, J=7.34 Hz, 1 H)
667			993.0	(600 MHz):0.78 - 0.88 (m, 6 H) 0.97 - 1.02 (m, 3 H) 1.09 - 1.13 (m, 6 H) 1.12 - 1.23 (m, 12 H) 1.28 (d, J=6.88 Hz, 3 H) 1.34 (s, 3 H) 1.56 - 1.70 (m, 3 H) 1.72 - 1.90 (m, 2 H) 1.91 - 1.97 (m, 1 H) 2.10 - 2.24 (m, 2 H) 2.23 - 2.31 (m, 2 H) 2.27 (s, 6 H) 2.35 - 2.41 (m, 2 H) 2.38 (s, 3 H) 2.41 - 2.68 (m, 9 H) 2.72 - 2.77 (m, 1 H) 2.79 - 2.83 (m, 1 H) 2.94 - 3.00 (m, 1 H) 3.16 - 3.20 (m, 1 H) 3.22 - 3.25 (m, 3 H) 3.35 (s, 3 H) 3.37 - 3.45 (m, 1 H) 3.54 - 3.60 (m, 1 H) 3.68 - 3.71 (m, 1 H) 3.79 - 3.82 (m, 3 H) 4.03 - 4.13 (m, 1 H) 4.32 - 4.39 (m, 1 H) 4.41 - 4.46 (m, 1 H) 4.47 - 4.53 (m, 1 H) 4.70 - 4.81 (m, 1 H) 4.85 (d, J=5.04 Hz, 1 H) 6.83 - 6.87 (m, 1 H) 6.93 (t, J=6.88 Hz, 1 H) 7.16 - 7.22 (m, 1 H) 7.32 - 7.36 (m, 1 H)
668			951.1	(600 MHz):0.76 - 0.89 (m, 6 H) 1.06 - 1.37 (m, 24 H) 1.58 - 1.95 (m, 5 H) 2.05 - 2.27 (m, 5 H) 2.27 (s, 6 H) 2.33 - 2.40 (m, 5 H) 2.42 - 2.77 (m, 8 H) 2.78 - 2.86 (m, 1 H) 2.89 - 2.98 (m, 1 H) 3.14 - 3.25 (m, 4 H) 3.31 - 3.35 (m, 3 H) 3.35 - 3.45 (m, 1 H) 3.45 - 3.55 (m, 1 H) 3.61 - 3.76 (m, 2 H) 4.07 - 4.19 (m, 1 H) 4.34 - 4.47 (m, 2 H) 4.73 - 4.85 (m, 1 H) 4.86 - 4.91 (m, 1 H) 6.68 - 6.77 (m, 2 H) 6.83 - 6.86 (m, 1 H) 7.13 (t, J=7.79 Hz, 1 H)

Example 664

[1324] 

(1) By using the compound obtained in Example 104, (1) (740 mg) as a starting material, a 4"-hydroxy compound (630 mg) was obtained in the same manner as that of Example 126, (1).

(2) By using the compound obtained in (1) mentioned above (100 mg) as a starting material, an imidazolylcarbonyl compound (109 mg) was obtained in the same manner as that of Example 126, (2).

(3) By using the compound obtained in (2) mentioned above (30 mg) and the compound obtained in Reference Example 106 (10.1 mg) as starting materials, the compound shown in Table 16 (21 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 665

[1325] By using the compound obtained in Example 664, (2) (30 mg) and the compound obtained in Reference Example 131 (10.1 mg) as starting materials, the compound shown in Table 16 (17 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 666

[1326] By using the compound obtained in Example 664, (2) (30 mg) and the compound obtained in Reference Example 54 (12.3 mg) as starting materials, the compound shown in Table 16 (21 mg) was obtained in the same manners as those of Example 126, (3) and Example 7, (4).

Example 667

[1327] 

(1) By using the compound obtained in Example 664, (1) (500 mg) as a starting material, a ketone compound (401 mg) was obtained in the same manner as that of Example 113, (2).

(2) By using the compound obtained in (1) mentioned above (200 mg) as a starting material, an epoxy compound (146 mg) was obtained in the same manner as that of Example 172, (1).

(3) By using the compound obtained in (2) mentioned above (142 mg) as a starting material, a deprotected compound (106 mg) was obtained in the same manner as that of Example 7, (4).

(4) By using the compound obtained in (3) mentioned above (30 mg) and the compound obtained in Reference Example 54 (43.4 mg) as starting materials, the compound shown in Table 16 (14.2 mg) was obtained in the same manner as that of Example 168, (2).

Example 668

[1328] By using the compound obtained in Example 667, (2) (30 mg) and the compound obtained in Reference Example 106 (35.1 mg) as starting materials, the compound shown in Table 16 (10.3 mg) was obtained in the same manner as that of Example 168, (2).

[1329] The "cladinosyl" mentioned in the aforementioned tables means a group represented by the following formula.

[1330] 

Syntheses of Examples 669 to 675

[1331] Preparation methods of compounds represented by the formula (AD) having R^{1 A D} and R^{2 A D} defined in Table 17 are shown below.

[1332] 

[1333] 

[Table 17-1]

Example	R1AD	R2AD	MS (M+H)	1H-NMR, CDCl3, δ (ppm)
669			833.7	(500 MHz) : 0.81 (d, J=6.86 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 0.95 (d, J=6.03 Hz, 3 H) 1.05 - 1.28 (m, 11 H) 1.10 (d, J=7.40 Hz, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.31 (s, 3 H) 1.48 - 1.91 (m, 5 H) 1.98 - 2.10 (m, 2 H) 2.11 - 2.57 (m, 7 H) 2.18 (s, 6 H) 2.29 (s, 6 H) 2.35 (s, 3 H) 2.65 - 2.73 (m, 1 H) 2.74 - 2.83 (m, 2 H) 2.85 - 2.94 (m, 1 H) 3.17 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.29 (s, 3 H) 3.33 - 3.45 (m, 1 H) 3.47 - 3.58 (m, 1 H) 3.71 (d, J=8.23 Hz, 1 H) 4.13 - 4.22 (m, 1 H) 4.34 - 4.42 (m, 2 H) 4.57 - 4.66 (m, 1 H) 4.97 (d, J=4.66 Hz, 1 H)
670			833.6	(500 MHz) : 0.81 (d, J=7.13 Hz, 6 H) 0.89 (t, J=7.40 Hz, 3 H) 0.99 (d, J=5.48 Hz, 3 H) 1.05 - 1.28 (m, 8 H) 1.09 (d, J=7.40 Hz, 3 H) 1.12 (s, 3 H) 1.21 (d, J=6.03 Hz, 3 H) 1.31 (s, 3 H) 1.48 - 1.94 (m, 5 H) 1.97 - 2.04 (m, 1 H) 2.09 - 2.55 (m, 8 H) 2.20 (s, 6 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.64 - 2.74 (m, 1 H) 2.74 - 2.81 (m, 1 H) 2.90 (d, J=14.54 Hz, 1 H) 2.95 (d, J=13.16 Hz, 1 H) 3.16 - 3.23 (m, 1 H) 3.23 (s, 3 H) 3.28 (s, 3 H) 3.34 - 3.45 (m, 1 H) 3.46 - 3.56 (m, 1 H) 3.72 (d, J=7.68 Hz, 1 H) 4.12 - 4.22 (m, 1 H) 4.32 (q, J=6.40 Hz, 1 H) 4.38 (d, J=7.40 Hz, 1 H) 4.57 - 4.68 (m, 1 H) 4.96 (d, J=4.94 Hz, 1 H)
671			859.6	(500 MHz): 0.81 (d, J=6.88 Hz, 6 H) 0.89 (t, J=7.45 Hz, 3 H) 1.03 - 1.28 (m, 20 H) 1.31 (s, 3 H) 1.46 - 1.94 (m, 9 H) 2.01 - 2.33 (m, 6 H) 2.29 (s, 6 H) 2.36 (s, 3 H) 2.38 - 2.69 (m, 5 H) 2.73 - 2.84 (m, 3 H) 2.90 (d, J=15.29 Hz, 1 H) 3.09 - 3.22 (m, 3 H) 3.23 (s, 3 H) 3.28 (s, 3 H) 3.36 - 3.44 (m, 1 H) 3.46 - 3.55 (m, 1 H) 3.71 (d, J=8.41 Hz, 1 H) 4.15 - 4.23 (m, 1 H) 4.32 - 4.40 (m, 2 H) 4.57 - 4.67 (m, 1 H) 4.97 (d, J=4.97 Hz, 1 H)

[1334] 

[Table 17-2]

672			896.4	mixture of diastereomers(400 MHz) : 0.80 - 0.84 (m, 6 H) 0.88 - 0.93 (m, 3 H) 1.03 - 1.37 (m, 23 H) 2.06 - 2.50 (m, 19 H) 2.61- 2.96 (m, 6 H) 3.16 - 3.68 (m, 15 H) 3.80 - 3.83 (m, 4 H) 4.06 (m, 1 H) 4.36 - 4.42 (m, 2 H) 4.65 (m, 1 H) 4.79 (d, J=4.9 Hz, 1 H) 6.82 - 6.94 (m, 2 H) 7.18 - 7.23 (m, 2 H)
673			868.3	(400 MHz) : 0.82 (d, J=6.9 Hz, 3 H) 0.82 (d, J=6.9 Hz, 3 H) 0.90 (t, J=7.3 Hz, 3 H) 1.05 (s, 3 H) 1.08 (d, J=7.3 Hz, 3 H) 1.15 - 1.20 (m, 11 H) 1.32 (s, 3 H) 1.50 - 1.89 (m, 10 H) 2.00 - 2.46 (m, 15 H) 3.20 (dd, J=10.3, 7.1 Hz, 1 H) 3.23 (s, 3 H) 3.26 (s, 3 H) 3.50 (m, 1 H) 3.62 (d, J=13.4 Hz, 1 H) 3.68 (d, J=8.1 Hz, 1 H) 3.84 (s, 3 H) 3.85 (d, J=13.4 Hz, 1 H) 4.14 (m, 1 H) 4.37 (d, J=7.1Hz, 1 H) 4.39 (q, J=6.4 Hz, 1 H) 4.62 (m, 1 H) 4.96 (m, 1 H) 6.85 - 6.93 (m, 2 H) 7.15 - 7.26 (m, 2 H)
674			882.3	(400 MHz) : 0.81 (d, J=7.0 Hz, 3 H) 0.81 (d, J=7.0 Hz, 3 H) 0.84 (t, J=7.3 Hz, 3 H) 1.08 - 1.17 (m, 17 H) 1.30 (s, 3 H) 1.35 (d, J=6.9 Hz, 3 H) 1.43 - 2.05 (m, 10 H) 2.13 - 2.46 (m, 15 H) 2.73 - 2.94 (m, 3 H) 3.18 (dd, J=10.0, 7.3 Hz, 1 H) 3.23 (s, 3 H) 3.26 (s, 3 H) 3.34 - 3.45 (m, 2 H) 3.67 (d, J=7.8 Hz, 1 H) 3.83 (s, 3 H) 4.02 (m, 1 H) 4.08 - 4.14 (m, 1 H) 4.30 (q, J=6.4 Hz, 1 H) 4.35 (d, J=7.4 Hz, 1 H) 4.62 (m, 1 H) 4.96 (m, 1 H) 6.84 - 6.94 (m, 2 H) 7.18 - 7.24 (m, 2 H)
675			910.4	(400 MHz) : 0.82 (d, J=7.1 Hz, 3 H) 0.82 (d, J=7.1 Hz, 3 H) 0.90 (t, J=7.4 Hz, 3 H) 1.08 - 1.44 (m, 24 H) 1.50 - 1.80 (m, 10 H) 1.95 - 2.60 (m, 18 H) 2.72 - 2.93 (m, 3 H) 3.20 (m, 1 H) 3.23 (s, 3 H) 3.32 (s, 3 H) 3.39 (m, 2 H) 3.72 (d, J=8.1 Hz, 1 H) 3.85 (s, 3 H) 4.15 - 4.25 (m, 2 H) 4.35 - 4.40 (m, 2 H) 4.63 (m, 1 H) 4.99 (m, 1 H) 6.84 - 6.95 (m, 2 H) 7.24 - 7.34 (m, 2 H)

Example 669

[1335] By using the compound obtained in Example 368, (1) (30 mg) and 1-dimethylamino-2-propylamine (21.0 mg) as starting materials, the compound shown in Table 17 (8.1 mg) was obtained in the same manner as that of Example 368, (2).

Example 670

[1336] By using the compound obtained in Example 368, (1) (30 mg) and 1-dimethylamino-2-propylamine (21.0 mg) as starting materials, a diastereomer of the compound of Example 669 shown in Table 17 (11.0 mg) was obtained in the same manner as that of Example 368, (2).

Example 671

[1337] By using the compound obtained in Example 368, (1) (30 mg) and (S)-(-)-2-aminomethyl-1-ethylpyrrolidine (26.3 mg) as starting materials, the compound shown in Table 17 (21.7 mg) was obtained in the same manner as that of Example 368, (2).

Example 672

[1338] By using the compound obtained in Example 412, (1) (30 mg) and the compound obtained in Reference Example 220 (32 mg) as starting materials, the compound shown in Table 17 (25 mg) was obtained in the same manner as that of Example 535.

Example 673

[1339] 

(1) By using the compound obtained in Example 168, (1) (25 mg) and 2-methoxybenzylamine (23 µl) as starting materials, an amine compound (29 mg) was obtained in the same manner as that of Example 535.

(2) By using the compound obtained in (1) mentioned above (19 mg) as a starting material, the compound shown in Table 17 (13 mg) was obtained in the same manner as that of Example 7, (4).

Example 674

[1340] 

(1) By using the compound obtained in Example 168, (1) (26 mg) and (1S)-(2-methoxyphenyl)ethanamine (26 mg) obtained by the method described in the patent document (Japanese Patent Unexamined Publication No. 54-154724) as starting materials, an amine compound (30 mg) was obtained in the same manner as that of Example 535.

(2) By using the compound obtained in (1) mentioned above (19 mg) as a starting material, the compound shown in Table 17 (13 mg) was obtained in the same manner as that of Example 7, (4).

Example 675

[1341] By using the compound obtained in Example 368, (1) (33 mg) and the compound obtained in Reference Example 54, (2) (40 mg) as starting materials, the compound shown in Table 17 (21 mg) was obtained in the same manner as that of Example 535.

Syntheses of Examples 676 to 778

[1342] By using the compound obtained in Example 368, (1) and amine reagents as starting materials, compounds represented by the formula (AE) having R defined in Table 18 were obtained in the same manner as that of Example 368, (2).

[1343] 

[1344] 

[Table 18-1]

Example	R	ESI MS (M+H)
676		788.93
677		802.97
678		873.99
679		849.00
680		832.97
681		820.00
682		819.00
683		790.97

[1345] 

[Table 18-2]

684		804.99
685		820.99
686		819.01
687		822.97
688		805.01
689		819.01
690		776.95
691		806.98
692		808.02

[1346] 

[Table 18-3]

693		790.98
694		835.01
695		806.98
696		889.04
697		822.96
698		820.99
699		850.01

[1347] 

[Table 18-4]

700		802.99
701		836.97
702		835.01
703		802.98
704		820.99
705		835.00
706		835.02
707		806.98

[1348] 

[Table 18-5]

708		820.99
709		821.00
710		806.99
711		847.00
712		832.99
713		846.02
714		836.98

[1349] 

[Table 18-6]

715		832.99
716		862.01
717		822.97
718		822.97
719		846.01
720		846.99
721		860.04

[1350] 

[Table 18-7]

722		860.05
723		835.01
724		866.97
725		806.98
726		833.99
727		836.01
728		836.99

[1351] 

[Table 18-8]

729		788.97
730		836.97
731		821.00
732		862.06
733		860.99
734		835.02

[1352] 

[Table 18-9]

735		860.03
736		835.00
737		835.01
738		836.99
739		806.97
740		880.01
741		835.00

[1353] 

[Table 18-10]

742		835.00
743		820.00
744		862.00
745		835.00
746		834.99
747		850.00
748		850.01

[1354] 

[Table 18-11]

749		866.96
750		806.97
751		846.01
752		867.03
753		888.11
754		821.04
755		821.04

[1355] 

[Table 18-12]

756		819.06
757		890.09
758		860.05
759		849.04
760		861.00
761		889.09
762		860.08

[1356] 

[Table 18-13]

763		874.09
764		860.08
765		835.06
766		835.05
767		865.03 (APCI)
768		890.08
769		886.09

[1357] 

[Table 18-14]

770		834.03
771		846.03
772		848.04
773		862.06
774		890.08
775		876.02

[1358] 

[Table 18-15]

776		874.07
777		878.01
778		819.04

Syntheses of Examples 779 to 822

[1359] By using the compound obtained in Example 412, (1) and amine reagents as starting materials, compounds represented by the formula (AF) having R defined in Table 19 were obtained in the same manner as that of Example 368, (2).

[1360] 

[1361] 

[Table 19-1]

Example	R	ESI MS (M+H)
779		882.94
780		839.94
781		853.97
782		839.95
783		839.95
784		868.98
785		868.98

[1362] 

[Table 19-2]

786		868.99
787		883.00
788		868.98
789		853.99
790		868.99

[1363] 

[Table 19-3]

791		853.99
792		881.00
793		880.99
794		882.03
795		884.97

[1364] 

[Table 19-4]

796		855.00
797		869.00
798		883.02
799		868.03
800		872.00

[1365] 

[Table 19-5]

801		883.03
802		883.02
803		854.02
804		869.02
805		865.01

[1366] 

[Table 19-6]

806		865.02
807		883.03
808		883.03
809		883.03
810		873.95

[1367] 

[Table 19-7]

811		883.03
812		883.04
813		883.03
814		881.02
815		881.02

[1368] 

[Table 19-8]

816		844.99
817		857.05
818		858.99
819		871.04
820		857.03

[1369] 

[Table 19-9]

821		871.05
822		888.99

Test Example 1 (in vitro antibacterial activity)

[1370] In vitro antibacterial activities of the compounds of the present invention against various test bacteria were measured according to the microbroth dilution method (NCCLS method). As test compounds, the compounds of Examples 7, 23, 114, 126, 131, 210, 214, 231, 257, 261, 287, 363, 366, 563 and Comparative agent 1: clarithromycin were used. The test bacteria used are shown in Table 20. The results are shown as MIC values (minimum inhibitory concentration, µg/ml) in Table 21.

[1371] 

[Table 20]

Test bacteria	Symbols of bacteria
H. influenzae ATCC 43095	A
S. pneumoniae ATCC 49619	B
S. pneumoniae 205	C

[1372] 

[Table 21]

Compound	A	B	C
Comparative agent 1	4	0.03	>128
Example 7	1	0.03	>128
Example 23	4	0.03	8
Example 114	8	0.016	0.06
Example 126	4	0.06	0.03
Example 131	16	0.03	0.12
Example 210	4	0.06	32
Example 214	1	0.03	>128
Example 231	8	0.06	2
Example 257	8	0.03	4
Example 261	4	0.12	64
Example 287	8	0.06	0.12
Example 363	2	0.12	4
Example 366	4	0.12	2
Example 563	16	0.25	64

Industrial Applicability

[1373] The compounds of the present invention have superior antibacterial activity against Hemophilus influenzae, erythromycin resistant pneumococci and the like, and therefore, they can be used as therapeutic agents of infectious diseases.

Claims

1. A 10a-azalide compound represented by the formula (I):

{wherein, in the formula (I), R¹ is:
hydrogen atom,
a halogen atom, or
a C_1-10 alkyl group which may be substituted,
R² and R³ combine together to represent oxo group, or
one of them is hydrogen atom, and the other is:

hydrogen atom,

hydroxyl group,

a protected hydroxyl group,

a group represented by the formula -X⁰³¹-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-R⁰³¹,

a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-A⁰³³-X⁰³⁴-R⁰³¹,

or a group represented by the formula:



wherein X⁰³¹ is:

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OHO₂-, or

a group represented by the formula -OCON(R²⁰)-,

one of R³² and R³³ is hydrogen atom, and the other is:

hydrogen atom,

amino group,

hydroxyl group,

a protected hydroxyl group,

a group represented by the formula -OCON(R²⁴)R²⁵ (in the formula, R²⁴ and R²⁵ both represent hydrogen atom, or represent groups which combine to form a cyclic amino group together with the adjacent nitrogen atom),

a group represented by the formula -X³³¹-R³³¹,

a group represented by the formula -X³³¹-A³³¹-X³³²-R³³¹,

a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-R³³¹, or

a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-A³³³-X³³⁴-R³³¹,
wherein X³³¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-,

a group represented by the formula -OCON(R²⁰)-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-,

or one of R³² and R³³ is hydroxyl group, and the other is:

a group represented by the formula -CH₂NH₂,

a group represented by the formula -X³³⁵-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-R³³²,

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-R³³², or

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-A³³⁶-X³³⁸-R³³²,
wherein X³³⁵ is:

a single bond,

a group represented by the formula -(CH₂)_n-N(R²⁰)-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CO-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CO₂-,

a group represented by the formula -(CH₂)_n-N(R²⁰)CON(R²¹)-,

a group represented by the formula -(CH₂)_n-N(R²⁰)O-,

a group represented by the formula -(CH₂)_n-OCON(R²⁰)-,

a group represented by the formula -(CH₂)_n-ON(R²⁰)CO-,

a group represented by the formula -(CH₂)_n-O-,

a group represented by the formula -(CH₂)_n-OCO-,

a group represented by the formula -(CH₂)_n-OCO₂-,

a group represented by the formula -(CH₂)_n-OC(NR²⁰)-, or

a group represented by the formula -(CH₂)_n-S(O)_p-,

or R³² and R³³ combine together to represent:

oxo group,

oxime group,

a group represented by the formula =N-X³³⁹-R³³³,

a group represented by the formula =N-X³³⁹-A³³⁷-X³⁴⁰-R³³³,

a group represented by the formula =N-X³³⁹-A³³⁷-X³⁴⁰-A³³⁸-X³⁴¹-R³³³,

a group represented by the formula =N-X³³⁹-A³³⁷-X³⁴⁰-A³³⁸-X³⁴¹-A³³⁹-X³⁴²-R³³³, or a group represented by the formula:



wherein X³³⁹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-, and

R³³⁴ is:

a group represented by the formula -SH,

a group represented by the formula -OH,

a group represented by the formula -X³⁴³-R³³⁵,

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-R³³⁵,

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-A³⁴¹-X³⁴⁵-R³³⁵, or

a group represented by the formula -X³⁴³-A³⁴⁰-X³⁴⁴-A³⁴¹-X³⁴⁵-A³⁴²-X³⁴⁶-R³³⁵,
wherein X³⁴³ is:

a single bond,

a group represented by the formula -S-, or

a group represented by the formula -(CH₂)_n CO-,

R⁴ is:

hydrogen atom,

a group represented by the formula -CONHCO₂Me

a group represented by the formula -X⁰⁴¹-R⁰⁴¹,

a group represented by the formula -X⁰⁴¹-A⁰⁴¹-X⁰⁴²-R⁰⁴¹,

a group represented by the formula -X⁰⁴¹-A⁰⁴¹-X⁰⁴²-A⁰⁴²-X⁰⁴³-R⁰⁴¹, or

a group represented by the formula -X⁰⁴¹-A⁰⁴¹-X⁰⁴²-A⁰⁴²-X⁰⁴³-A⁰⁴³-X⁰⁴⁴-R⁰⁴¹,
wherein X⁰⁴¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CON(R²⁰)-, or

a group represented by the formula -CO₂-,

or R⁴ may combine with R⁶ to form cyclic carbonate [-CO₂-],

one of R⁵ and R⁶ is hydrogen atom, and the other is:

hydrogen atom,

hydroxylgroup,

a protected hydroxyl group,

amino group,

a protected amino group,

a halogen atom,

a group represented by the formula -OCONH₂,

a group represented by the formula -X⁰⁶¹-R⁰⁶¹,

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-R⁰⁶¹,

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-R⁰⁶¹, or

a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-A⁰⁶²-X⁰⁶³-A⁰⁶³-X⁰⁶⁴-R⁰⁶¹,

or may combine with R⁷ to form cyclic carbamate [-OCO-],
wherein X⁰⁶¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-,

a group represented by the formula -OCON(R²⁰)-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-,

a group represented by the formula -N(R²⁰)SO₂-, or

a group represented by the formula -CH₂N(R²⁰)-,

or R⁵ and R⁶ combine together to represent

oxo group,

oxime group,

a group represented by the formula =N-NH₂,

a protected oxime group,

a group represented by the formula =N-X⁰⁶⁵-R⁰⁶²,

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-R⁰⁶²,

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-R⁰⁶², or

a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-A⁰⁶⁶-X⁰⁶⁸-R⁰⁶²
wherein X⁰⁶⁵ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CO₂-,

a group represented by the formula -N(R²⁰)CON(R²¹)-, or

a group represented by the formula -N(R²⁰)SO₂-,

R⁷ is:

hydrogen atom,

hydroxyl group,

a protective group of amino group,

a group represented by the formula -X⁰⁷¹-R⁰⁷¹,

a group represented by the formula -X⁰⁷¹-A⁰⁷¹-X⁰⁷²-R⁰⁷¹, or

a group represented by the formula -X⁰⁷¹-A⁰⁷¹-X⁰⁷²-A⁰⁷²-X⁰⁷³-R⁰⁷¹, or

may combine with R¹⁰ to form cyclic carbamate [-CO₂CH₂-],
wherein X⁰⁷¹ is:

a single bond,

a group represented by the formula -O-,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -SO₂-,

R⁸ and R⁹, which are the same or different, represent:

hydrogen atom,

a group represented by the formula -X⁰⁸¹-R⁰⁸¹,

a group represented by the formula -X⁰⁸¹-A⁰⁸¹-X⁰⁸²-R⁰⁸¹, or

a group represented by the formula -X⁰⁸¹-A⁰⁸¹-X⁰⁸²-A⁰⁸²-X⁰⁸³-R⁰⁸¹,
wherein X⁰⁸¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

R¹⁰ and R¹¹, which are the same or different, represent

hydrogen atom,

a group represented by the formula -X¹⁰¹-R¹⁰¹,

a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-R¹⁰¹,

a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-A¹⁰²-X¹⁰³-R¹⁰¹, or

a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-A¹⁰²-X¹⁰³-A¹⁰³-X¹⁰⁴-R¹⁰¹,
wherein X¹⁰¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

R¹² is:

hydrogen atom,

a protective group of hydroxyl group,

a group represented by the formula -X¹²¹-R¹²¹,

a group represented by the formula -X¹²¹-A¹²¹-X¹²²-R¹²¹, or

a group represented by the formula -X¹²¹-A¹²¹-X¹²²-A¹²²-X¹²³-R¹²¹,
wherein X¹²¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

R¹³ and R¹⁴, which are the same or different, represent

hydrogen atom,

a protective group of amino group,

a group represented by the formula -X¹³¹-R¹³¹,

a group represented by the formula -X¹³¹-A¹³¹-X¹³²-R¹³¹, or

a group represented by the formula -X¹³¹-A¹³¹-X¹³²-A¹³²-X¹³³-R¹³¹,
wherein X¹³¹ is:

a single bond,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-, or

a group represented by the formula -CON(R²⁰)-,

R¹⁵ is:

hydrogen atom,

hydroxyl group,

a protected hydroxyl group,

a group represented by the formula -X¹⁵¹-R¹⁵¹,

a group represented by the formula -X¹⁵¹-A¹⁵¹-X¹⁵²-R¹⁵¹, or

a group represented by the formula -X¹⁵¹-A¹⁵¹-X¹⁵²-A¹⁵²-X¹⁵³-R¹⁵¹,
wherein X¹⁵¹ is:

a single bond,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-, or

a group represented by the formula -OCON(R²⁰)-,

X⁰³²,X⁰³³,X⁰³⁴,X³³²,X³³³,X³³⁴,X³³⁶,X³³⁷, X³³⁸,X³⁴⁰,X³⁴¹,X³⁴²,X³⁴⁴, X³⁴⁵,X³⁴⁶,X⁰⁴²,X⁰⁴³,X⁰⁴⁴,X⁰⁶²,X⁰⁶³,X⁰⁶⁴,X⁰⁶⁶,X⁰⁶⁷,X⁰⁶⁸,X⁰⁷²,X⁰⁷³, X⁰⁸²,X⁰⁸³,X¹⁰²,X¹⁰³,X¹⁰⁴,X¹²²,X¹²³,X¹³²,X¹³³,X¹⁵² and X¹⁵³ mentioned above, which are the same or different, represent

a single bond

a group represented by the formula -O-,

a group represented by the formula -OCO-,

a group represented by the formula -OCO₂-,

a group represented by the formula -OCON(R²⁰)-,

a group represented by the formula -S(O)_p-,

a group represented by the formula -SO₂N(R²⁰)-,

a group represented by the formula -OCS-,

a group represented by the formula -CO-,

a group represented by the formula -CO₂-,

a group represented by the formula -CON(R²⁰)-,

a group represented by the formula -CH=N-,

a group represented by the formula -CH=N-O-,

a group represented by the formula -CH=N(R²⁰)-,

a group represented by the formula -CH=N(R²⁰)O-,

a group represented by the formula -CH=N(R²⁰)N(R²¹)-,

a group represented by the formula -CH=N(OR²⁰)-,

a group represented by the formula -CH=N-N(R²⁰)R²¹-,

a group represented by the formula -CS-,

a group represented by the formula -C(S)O-,

a group represented by the formula -CSN(R²⁰)-,

a group represented by the formula -O-N=CH-,

a group represented by the formula -N=CH-,

a group represented by the formula -N(R²⁰)-,

a group represented by the formula -N(R²⁰)CO-,

a group represented by the formula -N(R²⁰)CS-,

a group represented by the formula -N(R²⁰)SO₂-,

a group represented by the formula -N(R²⁰)CO₂-, or

a group represented by the formula -N(R²⁰)CON(R²¹)-,

A⁰³¹,A⁰³²,A⁰³³,A³³¹,A³³²,A³³³,A³³⁴,A³³⁵,A³³⁶,A³³⁷,A³³⁸,A³³⁹,A³⁴⁰, A³⁴¹,A³⁴²,A⁰⁴¹,A⁰⁴²,A⁰⁴³,A⁰⁶¹,A⁰⁶²,A⁰⁶³,A⁰⁶⁴,A⁰⁶⁵,A⁰⁶⁶,A⁰⁷¹,A⁰⁷², A⁰⁸¹,A⁰⁸²,A¹⁰¹,A¹⁰²,A¹⁰³,A¹²¹,A¹²²,A¹³¹,A¹³²,A¹⁵¹ and A¹⁵² mentioned above, which are the same or different, represent

a divalent C_1-10 aliphatic hydrocarbon group which may be substituted with hydroxyl group,

an arylene group, or

a divalent heterocyclic group,

R⁰³¹,R³³¹,R³³²,R³³³,R³³⁵,R⁰⁴¹,R⁰⁶¹,R⁰⁶²,R⁰⁷¹,R⁰⁸¹,R¹⁰¹,R¹²¹,R¹³¹

and R¹⁵¹ mentioned above, which are the same or different, represent

a C_1-10 alkyl group which may be substituted,

a C_2-10 alkenyl group which may be substituted,

a C_2-10 alkynyl group which may be substituted,

a C_3-10 cycloalkyl group which may be substituted,

a C_3-10 cycloalkyl group condensed with an aryl group, which may be substituted,

an aryl group which may be substituted, or

a heterocyclic group which may be substituted,

substituents of the groups "which may be substituted" mentioned above each mean arbitrary 1 to 5 substituents selected from the following group of substituents, and the group of substituents consists of:

- carboxyl group,

- a halogen atom,

- oxo group,

- hydroxyl group,

- cyano group,

- nitro group,

- oxido group,

- sulfonic acid group, and

- thiol group,

as well as the following group which may be substituted with groups of the group A:

- a C_1-10 alkyl group,

- a C_2-12 alkenyl group,

- a C_2-12 alkynyl group,

- a C_3-10 cycloalkyl group,

- a C_1-10 alkoxy group,

- a C_1-10 hydroxyalkoxy group,

- a C_2-12 alkenyloxy group,

- a carboxy(C_1-6 alkyloxy) group,

- a cyano(C_1-6 alkyloxy) group,

- a C_1-10 alkylthio group,

- a C_1-6 alkylsulfonyl group,

- an arylsulfonyl group which may be substituted with a C_1-6 alkyl group or a halogen atom,

- a C_1-10 haloalkylthio group,

- a C_2-10 alkenylthio group,

- a (C_1-6 alkoxy)(C_1-6 alkyl) group,

- a (C_1-6 alkoxy)(C_1-6 alkoxy) group,

- a C_1-10 haloalkyl group,

- a C_2-12 alkanoyl group,

- a C_2-12 alkanoyloxy group,

- a (C_2-12 alkanoyloxy)(C_1-6 alkyl) group,

- a benzoyl group which may be substituted with 1 to 3 of halogen atoms or nitro groups,

- a C_2-6 alkanoylamino group,

- an aminosulfonyl group which may be substituted with 1 or 2 of C_1-6 alkyl groups,

- a C_1-6 alkylsulfonyl group,

- a C_1-6 alkylsulfonylamino group,

- a benzenesulfonylamino group which may be substituted with C_1-6 alkyl,

- succinimido group,

- maleimido group,

- phthalimido group,

- a C_2-10 alkoxycarbonyl group,

- a C_2-10 alkoxycarbonylalkoxy group,

- tri-(C_1-6 alkyl)silyloxy group,

- a group represented by the formula -N(R²²)R²³ (in the formula, R²² and R²³ each represent hydrogen atom, a C_1-6 alkyl group, a C_1-6 hydroxyalkyl group, a C_3-10 alkoxycarbonylalkyl group or a cyano(C_1-6 alkyl) group, or represent groups which combine to form, together with the adjacent nitrogen atom, a cyclic amino group, which may be substituted with "a C_1-6 alkyl group, a cyano(C_1-6 alkyl) group, a C_3-10 o cycloalkyl group, a C_2-6 alkanoyl group, benzoyl group, an aryloxy(C_2-6 alkanoyl) group which may be substituted with "a C_1-6 alkyl group or a C_1-6 alkoxy group", a (C_1-6 alkoxy)(C_1-6 alkyl) group, a C_2-6 alkoxycarbonyl group, oxo group, or hydroxyl group"),

- a group represented by the formula -CON(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),

- a group represented by the formula -OCON(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),

- a group represented by the formula -CH₂ N(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above),

- a group represented by the formula -O(CH₂)_m N(R²²)R²³ (in the formula, R²² and R²³ have the same meanings as those defined above), and

- "an aryl group, a heterocyclic group, an aryloxy group, an arylthio group, a heterocyclyloxy group or a heterocyclylthio group" which may be substituted with 1 to 5 of groups arbitrarily selected from the group consisting of "a C_{1 - 6} alkyl group, a C_1-6 haloalkyl group, a halogen atom, a C_{1 - 6} alkoxy group, an aminosulfonyl group which may be substituted with 1 or 2 of C_{1 - 6} alkyl groups, an aminosulfonylamino group which may be substituted with 1 or 2 of C_{1 - 6} alkyl groups, an amino(C_{1 - 6} alkyl) group which may be substituted with 1 or 2 of C_{1 - 6} alkyl groups, a saturated heterocyclic group, a C_{1 - 6} alkyl group substituted with a saturated heterocyclic group, carboxyl group, a C_{2 - 10} alkoxycarbonyl group, a C_{1 - 6} hydroxyalkyl group, cyano group, a cyano(C_{1 - 6} alkyl) group, an amino group which may be substituted with 1 or 2 of C_{1 - 6} alkyl groups, hydroxyl group, a C_{1 - 10} alkylthio group, a C_{1 - 6} alkylsulfonyl group, a C_{1 - 6} alkylsulfonylamino group and nitro group", which may be substituted with groups of the group A,

wherein group A consists of "an aryl group, a heterocyclic group, a heterocyclylthio group or an aryloxy group" which may be substituted with "a halogen atom, a C_{1 - 6} alkyl group, a hydroxy(C_{1 - 6} alkyl) group, hydroxyl group or nitro group", cyano group, cyanothio group, carboxyl group, hydroxyl group, a C_2-10 alkoxycarbonyl group, and a C_{1 - 10} alkoxy group, R²⁰ and R²¹ mentioned above, which are the same or different, represent a group suitably selected from hydrogen atom, and a C_{1 - 10} alkyl group which may be substituted with the substituents mentioned above, p mentioned above is an integer of 0 to 2, n mentioned above is 1 or 2, and m mentioned above is an integer of 2 to 4}, a pharmaceutically acceptable salt thereof, or a solvate thereof.

2. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 1, wherein R¹³ and R¹⁴ are methyl groups, and R¹⁵ is hydrogen atom.

3. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atom, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:



R⁴ is hydrogen atom, or
a group represented by the formula -R⁰⁴¹, one of R⁵ and R⁶ is hydrogen atom, and
the other is hydroxyl group, or R⁵ and R⁶ combine together to represent oxo group, oxime group, a protected oxime group,
a group represented by the formula =N-X⁰⁶⁵-R⁰⁶²,
a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-R⁰⁶²,
a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-R⁰⁶², or
a group represented by the formula =N-X⁰⁶⁵-A⁰⁶⁴-X⁰⁶⁶-A⁰⁶⁵-X⁰⁶⁷-A⁰⁶⁶-X⁰⁶⁸-R⁰⁶², and R⁷ is methyl group.

4. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

R⁴ is hydrogen atom, or
a group represented by the formula -R⁰⁴¹, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, amino group,
a group represented by the formula -OCONH₂,
a group represented by the formula -X⁰⁶¹ -R⁰⁶¹, or
a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-R⁰⁶¹, or R⁵ and R⁶ combine together to represent oxo group, oxime group,
a group represented by the formula =N-NH₂,
a group represented by the formula =N-O-R⁰⁶², or
a group represented by the formula =N-O-A⁰⁶⁴-X⁰⁶⁶-R⁰⁶², R⁷ is methyl group, one of R¹⁰ and R¹¹ is hydrogen atom, and the other is hydrogen atom,
a group represented by the formula -X¹⁰¹-R¹⁰¹, or
a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-R¹⁰¹, and X¹⁰¹ is a single bond, or
a group represented by the formula -CO₂-.

5. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

R⁴ is hydrogen atom, methyl group, or
a group represented by the formula -CONHCO₂Me, R⁷ is methyl group, one of R⁵ and
R⁶ is hydrogen atom, and the other is hydroxyl group, one of R¹⁰ and R¹¹ is hydrogen atom, and the other is hydrogen atom,
a group represented by the formula -X¹⁰¹-R¹⁰¹, or
a group represented by the formula -X¹⁰¹-A¹⁰¹-X¹⁰²-R¹⁰¹, and X¹⁰¹ is a single bond, or
a group represented by the formula -CO₂-.

6. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is hydroxyl group,
a group represented by the formula -OCO-R⁰³¹, or
a group represented by the formula -OCO-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-A⁰³³-X⁰³⁴-R⁰³¹,
or R² and R³ combine together to represent oxo group, R⁴ and R⁷ are methyl groups, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, one of R¹⁰ and
R¹¹ is hydrogen atom, and the other is ethyl group, or
a group represented by the formula -A¹⁰¹-X¹⁰²-R¹⁰¹.

7. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

one of R³² and R³³ is hydrogen atom, and the other is hydroxyl group, amino group,
a group represented by the formula -X³³¹-A³³¹-X³³²-R³³¹, or
a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-R³³¹, X³³¹ is:

a group represented by the formula -OCO-, or

a group represented by the formula -OCONH-, or one of R³² and R³³ is hydroxyl group, and the other is methyl group, or

a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-R³³², X³³⁵ is:

a group represented by the formula -CH₂-NH-, or

a group represented by the formula -CH₂-NHCO-, or R³² and R³³ combine together to represent oxo group, or oxime group, R⁴ is hydrogen atom, or methyl group, R⁷ is methyl group, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, or R⁵ and R⁶ combine together to represent oxo group, or oxime group, one of R¹⁰ and

R¹¹ is hydrogen atom, and the other is hydrogen atom, methyl group, ethyl group, or cyanopropyl group.

8. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:



or
a group represented by the formula -OCO-R⁰³¹, R⁴ and R⁷ are methyl groups, one of R⁵ and R⁶ is hydrogen atom, and the other is amino group,
a group represented by the formula -OCONH₂,
a group represented by the formula -X⁰⁶¹-R⁰⁶¹, or
a group represented by the formula -X⁰⁶¹-A⁰⁶¹-X⁰⁶²-R⁰⁶¹, or R⁵ and R⁶ combine together to represent oxo group, oxime group,
a group represented by the formula =N-NH₂,
a group represented by the formula =N-O-R⁰⁶², or
a group represented by the formula =N-O-A⁰⁶⁴-X⁰⁶⁶-R⁰⁶², one of R¹⁰ and R¹¹ is hydrogen atom, and the other is hydrogen atom,
a group represented by the formula -R¹⁰¹, or
a group represented by the formula -A¹⁰¹-X¹⁰²-R¹⁰¹.

9. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, R² and R³ combine together to represent oxo group, or one of them is hydrogen atom, and the other is a group represented by the formula:

or
a group represented by the formula -OCO-R⁰³¹, R⁴ is methyl group, one of R⁵ and R⁶ is hydrogen atom, and the other combines with R⁷ to form cyclic carbamate [-OCO-], one of R¹⁰ and R¹¹ is hydrogen atom, and the other is ethyl group, or
a group represented by the formula -A¹⁰¹-X¹⁰²-R¹⁰¹.

10. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, R² and R³ combine together to represent oxo group, or one of them is hydrogen atom, and the other is a group represented by the formula:

R⁴ is:

a group represented by the formula -R⁰⁴¹, one of R⁵ and R⁶ is hydrogen atom, and

the other is hydroxyl group, R⁷ is methyl group, or may combine with one of R⁵ and
R⁶ to form cyclic carbamate [-OCO-], one of R¹⁰ and R¹¹ is hydrogen atom, and the other is ethyl group.

11. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

one of R³² and R³³ is hydrogen atom, and the other is amino group, hydroxyl group, a group represented by the formula -OCON(R²⁴)R²⁵ (in the formula, R²⁴ and R²⁵ both represent hydrogen atom, or represent groups which combine to form a cyclic amino group together with the adjacent nitrogen atom),
a group represented by the formula -X³³¹-R³³¹,
a group represented by the formula -X³³¹-A³³¹-X³³²-R³³¹, or
a group represented by the formula -X³³¹-A³³¹-X³³²-A³³²-X³³³-A³³³-X³³⁴-R³³¹,
R⁴ and R⁷ are methyl groups, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, one of R¹⁰ and R¹¹ is hydrogen atom, and the other is ethyl group.

12. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

one of R³² and R³³ is hydroxyl group, and the other is:
a group represented by the formula -CH₂NH₂,
a group represented by the formula -X³³⁵-R³³²,
a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-R³³², or
a group represented by the formula -X³³⁵-A³³⁴-X³³⁶-A³³⁵-X³³⁷-R³³², R⁴ and R⁷
are methyl groups, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, one of R¹⁰ and R¹¹ is hydrogen atom, and the other is ethyl group.

13. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

R³² and R³³ combine together to represent a group represented by the formula:



R³³⁴ is:

a group represented by the formula -SH, or

a group represented by the formula -OH, R⁴ and R⁷ are methyl group, one of R⁵ and

R⁶ is hydrogen atom, and the other is hydroxyl group, one of R¹⁰ and R¹¹ is hydrogen atom, and the other is ethyl group.

14. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

R⁴ is methyl group, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, R⁷ is:

a group represented by the formula -R⁰⁷¹, one of R¹⁰ and R¹¹ is hydrogen atom, and

the other is ethyl group.

15. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹, R⁸, R⁹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is hydroxyl group, or a group represented by the formula:



R⁴ is methyl group, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, R⁷ combines with R¹⁰ to form cyclic carbamate [-CO₂ CH₂-], and R¹¹ is hydrogen atom.

16. The 10a-azalide compound, pharmaceutically acceptable salt thereof, or solvate thereof according to claim 2, wherein R¹ and R¹² are hydrogen atoms, one of R² and R³ is hydrogen atom, and the other is a group represented by the formula:

R⁴ is methyl group, one of R⁵ and R⁶ is hydrogen atom, and the other is hydroxyl group, R⁷ is methyl group, or hydroxyl group, one of R⁸ and R⁹ is hydrogen atom, and the other is methyl group, one of R¹ and R¹¹ is hydrogen atom, and the other is methyl group, or ethyl group.

17. A compound represented by the formula (II):

(wherein, in the formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R¹², R¹³, R¹⁴ and R¹⁵ have the same meanings as those defined above except for the case where R⁶ combines with R⁷ to form cyclic carbamate [-OCO-]).

Amended claims

Amended claims under Art. 19.1 PCT

1. A 10a-azalide compound represented by the formula (I):

{wherein, in the formula (I), R¹ is:
hydrogen atom,
a halogen atom, or
a C_{1 - 10} alkyl group which may be substituted, R² and R³ combine together to represent oxo group, or
one of them is hydrogen atom, and the other is:
hydrogen atom,
hydroxyl group,
a protected hydroxyl group,
a group represented by the formula X⁰³¹-R⁰³¹,
a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-R⁰³¹,
a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³⁸-R⁰³¹,
a group represented by the formula -X⁰³¹-A⁰³¹-X⁰³²-A⁰³²-X⁰³³-A⁰³³-X⁰³⁴-R⁰³¹,
or a group represented by the formula:

wherein X⁰³¹ is:

a group represented by the formula -O-,